Vacation Rentals By Owner In Gloucester, MA

$442.06

Long Beach Suites: 3 Mins Toes To Sand!

Gloucester, Massachusetts, United States

Summary:brbrRecently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in one of our two bedroom apartment suites. Expertly built with summer visitors in mind.brbrbrbrLong Beach Suites is just steps away from Long Beach in Rockport and only ten minutes to Good Harbor. brbrbrbrPhotos may not be of exact apartment.brbrbrbrThe Space:brbrRecently built, Long Beach Suites, is ready to welcome you this summer. With some views from decks of Long Beach, come stay in one of our two bedroom apartment suites. Expertly being built with summer visitors in mind.brbrbrbrEach two bedroom suites sleep six guests each, each bedroom has a king size bed and there's a pull out queen sofa in the living room. brbrbrbrFull bathroom with tub/shower combo. brbrbrbrFull kitchen with kitchen island, induction flat top, and dishwasher. The kitchen is stocked with all the cooking/serving necessities including: cookware, pots, pans, plates, cups, and silverware. Four to six guests can eat at the dining table, four can eat at the kitchen counter. brbrbrbrDepending on your suite you will have a private deck or patio for you to enjoy. brbrbrbrOther things to get excited about: brbr-The two bedrooms and main living room each have TVs with streaming capabilities ONLY and no cable.brbr-Vinyl floors throughoutbrbr-In suite washer/dryerbrbr-Parking for up to two cars. brbr-Brand new top of the line energy efficient split heat/acbrbr-For protection, there are cameras throughout the common areas. Such security cameras are capable of recording video and audio and may have such features activated during your stay. Occupants shall not remove, alter, or otherwise utilize the cameras.brbrbrbrGuest Access:brbrEverything you need for a great stay, toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!brbrbrbrOther Things to Note:brbrWe are delighted to host you for your upcoming stay! We have expertly prepared and furnished each guest suite with lots of love and attention. brbrbrbrWhile you are staying with us: brbr-No parties.brbr-Please be mindful of our neighbors by keeping noise to a normal level, reducing noise after 9:00pm, and not lingering in front of the entrance. brbr-We ask that guests be off any exterior spaces by 10PM on the weekdays and 11PM on the weekends. This is not a curfew so you can come and go as you please past these times but you cannot hang out on exterior spaces past the posted times. brbr-Smoking is strictly prohibited both inside and outside within 50ft or near a window.brbr-No pets allowed, even for a short visit.brbr-No refunds to be given for shortened stays and for any cable, internet, WI-FI, heating, cooling, or power outages or other acts of nature.brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

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$1027.23

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Private Vacation Home

Tidebend: River views and gracious comfort

Gloucester, Massachusetts, United States

Welcome to Tidebend, your next Gloucester escape! This stunning 6-bedroom, 2.5-bath home overlooks the picturesque Annisquam River and offers a unique blend of craftsmanship, comfort, and convenience. Thoughtful custom woodwork and built-ins throughout the home highlight exceptional quality while adding character and function to the living spaces.brbrSpend your mornings on the inviting farmhouse-style front porch and soak in the peaceful water views from upstairs. Enjoy your evenings watching breathtaking sunsets.brbrLocated in a quiet neighborhood of Gloucester, Tidebend offers plenty of space for your family to enjoy this tranquil retreat.brbrNo smoking. No events or parties.

6

Bed

2

Bath

10

Sleeps

$684.16

/ Nightly

Private Vacation Home

Beautifully renovated OCEAN-FRONT luxury home on private beach

Gloucester, Massachusetts, United States

This is the house you've been looking for. Come and stay at this stunning custom-designed home on private Coffins Beach on the North Shore of Boston. You will have spectacular views and you are literally just steps away from the beach. brbrBeautifully renovated, our home has 5 bedrooms and 3 full bathrooms. The private master suite on the second floor includes a king-sized bed, a home office facing the ocean with desk space for two, a tiled bathroom and a walk in closet. The first floor has four bedrooms and two full bathrooms. Two of the bedrooms have queen beds. Two of the bedrooms each have a full bed and a bunk bed. brbrThe large living area on the first floor has a stunning cathedral ceiling and encompasses the kitchen, dining room and family room. The house has a lower deck with a grill and fire table and plenty of comfortable seating. The upper deck can be reached from the lower deck via a spiral staircase or from the master bedroom. It is the perfect spot to watch the sun set.brbrThe gorgeous private beach is 1.5 miles long and at low tide it is 150 yards wide. It's a perfect beach to walk or run on. The sand is soft and clean, the water is crystal clear and a collector's paradise for sand dollars. The beach side of the house is facing north and you will never tire of the beautiful sunrises and sunsets.

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$1633.81

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Private Vacation Home

Golden Sands at Good Harbor: Just walk across the street to the beach.

Gloucester, Massachusetts, United States

Golden Sands is the quintessential turn of the century Gloucester beach cottage. With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave this amazing beach house.brbrThe main level includes the living room which opens to the verandah and deck, dining room, kitchen, study and half bath. The comfortable eat-in kitchen with walk-in pantry is well stocked with everything necessary to prepare meals for 12 people including a dishwasher, 5 burner gas stove, plenty of dishware, and a large capacity washer and dryer.brbrThe second level has 4 bedrooms and 2 full baths (one with a tub & shower off the hall). Two single rooms have ocean views while the master (with twin beds) has an ensuite bathroom with tub and a door to a lovely private deck. The beds in the single bedrooms are oversized singles.brbrThe third floor has 3 more bedrooms (with 6 single beds in total) and a full bath with a tub, as well as commanding views.brbrLeave your car in the driveway and walk to the beach and experience summer like you never have before! After the beach, rinse off in the outdoor shower (with hot and cold water) and relax in the shaded yard and then make a quick dinner using the natural gas Weber grill. You can even use the outdoor mini fridge for cold al fresco beverages. Golden Sands has everything you could want in a summer vacation rental.brbrNote: An unobtrusive caretaker has use of the garage on the property for equipment storage. He will be accessing garage at the beginning and end of the work day, for maintenance reasons.

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$1000.12

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Private Vacation Home

Over By Good Harbor: Phenomenal views!

Gloucester, Massachusetts, United States

Just up the street from Good Harbor Beach, this well-appointed and perfectly located vacation rental is the ideal home base for your Gloucester beach vacation with family or friends. Over By Good Harbor sits prominently on a hill with abundant views of Good Harbor Beach and the sea beyond. The main floor wraparound porch is rivaled only by its large second-floor deck--the views only get better as you go up! The home is also just a short stroll down the street (0.2 miles) to Good Harbor's soft sand and sparkling waves.brbrEnjoy the ocean breezes from your front porch or the verdant lawn planted with tiger lilies on the backyard deck. Inside, the open concept living room invites to you to gather or relax with family or friends and enjoy the flat screen tv and gas fireplace. Just beyond is an adjacent den with queen pullout sofa, widescreen TV, air conditioning, and door to back yard. The large eat-in kitchen is fully equipped with center island, large table and has a door to a back deck, the perfect place to grill.brbrThe second floor has three bedrooms, including a large King primary with mini-split air conditioner, ensuite bath, walk in closet and sliders to the upper deck with superb views, another King bedroom with mini-split air conditioner, walk in closet and a smaller bedroom with double futon and window a/c. The washer and dryer are conveniently located at this level adjacent to another full bath with oval tub and shower.brbrThe garden level features a complete suite perfect for in-laws or an au pair.brbrThe two decks offer magnificent ocean views. The backyard features a gas grill, outdoor seating, and an outdoor shower to rinse off the sand after the beach.brbrWith Over by Good Harbor as your home base, you'll enjoy all that Gloucester and greater Cape Ann has to offer. When you are not at the beach, you'll find whale watching, fine cuisine, art galleries and shops all within a short drive.brbrNo pets. No smoking. No events or parties.

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$586.76

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Private Vacation Home

Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam

Gloucester, Massachusetts, United States

Greet each day with inspiring views of the Annisquam River from this charming vacation home and enjoy the most spectacular sunsets each evening. Terra Nova offers that get away from it all feeling, with a large verdant lawn, breathtaking water views, and comfortable furnishings. Inside, find an open-concept living and dining area with enormous picture windows letting in the light, along with two main-floor bedrooms, a full bath and kitchen. Downstairs, a large open-plan suite makes up the garden level.brbrFor those who prefer the outdoors, relax on the wraparound deck, take a swim, or launch a kayak into the river at high tide. You can also easily explore many of the local shops and restaurants that the area has to offer. The historic village of Annisquam is about a mile away, while Downtown Gloucester is four miles in one direction, and Rockport and Bearskin Neck and the Shalin Liu Performance Center are just five miles in the other direction.brbrMAIN FLOORbrbrLiving/Dining Room: A sun-drenched room with oversized windows, the space contains a flat screen TV, comfortable seating, and a dining table for six. There are also sliders out to the wraparound deck.brbrKitchen: An updated and well-equipped galley kitchen, with stainless appliances.brbrFull Bathroom 1: The glass walk-in shower has a fold-down seat for convenience and comfort.brbrBedroom 1: Master bedroom with a King bed.brbrBedroom 2: Contains a Full bed.brbrGARDEN LEVELbrbrBedroom 3: This room contains a Full bed and a daybed/sofa that can be made up as a Single.brbrFull Bathroom 2: Contains a stand-up shower.brbrLaundry: There is a utility room with a washer and dryer.brbrEXTERIOR The deck overlooks a spacious yard that slopes down to the river, where you can look for shells at low tide and swim at higher tides. There are also a gas grill, outdoor seating, and outdoor dining sets on the deck and on the patio.brbrPARKING There is parking for 2 cars.

3

Bed

2

Bath

6

Sleeps

$1268.59

/ Nightly

Private Vacation Home

Waterfront charming home in RockyNeck,Gloucester 4-bedroom

Gloucester, Massachusetts, United States

Your cozy getaway awaits in Gloucester at this fabulous house. With four bedrooms featuring a mix of two full beds, one queen, and a twin, guests have plenty of space to relax. Three bathrooms include a bathtub, making it easy to unwind after a day of exploring. The house stays comfortable with ocean breezes and some rooms have air conditioning, if needed. Enjoy the use of a tidal dock with beautiful sunrises for coffee or sunsets with a cocktail. Kayak or swim from the dock. At low tide, explore tidal pools or collect sea glass or walk to swim at the sandy beach. Watch the water birds that offer constant entertainment. Whether you’re gathering for a meal or enjoying quiet moments, this pleasant home offers a welcoming atmosphere. Fall in love with Gloucester and enjoy the magic it has to offer.

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$469.14

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Private Vacation Home

5-star home with quick walk to 2 beaches!!

Gloucester, Massachusetts, United States

brRenovated beach home, steps from two of New England's most beautiful beaches, Good Harbor and Long Beach! This beautiful 3 bedroom 2 bathroom home is the perfect place to relax and spend time with family or friends. It comfortably sleeps 6 people (1 King, 1 Queen, 2 twins) and also has an upper and lower level living room with large sectional sofas.brbrPrivate fenced in backyard, beautifully landscaped, with a gas grill, fire pit and new outdoor patio furniture (two large white picnic tables which will seat a minimum of 12 people). 8 Adirondack chairs surrounding gas fire pit. 4 lounge chairs. New outdoor shower just installed. The home is meticulously clean. You are sure to be instantly relaxed when you walk through the front door. 4 off street parking spaces available during your stay. Grill for outdoor cooking. brbrDid we say steps from beach ! Good Harbor is no more that a 5 minute walk from your front door, and Long Beach is only about a 7 minute walk. No need to park and pay, or wake up early to get a parking spot, both beaches are free since you are walking.brbrLocal attractions less than a mile from the home (most being within walking distance):brbr- Located between Good Harbor and Long Beach, be at the beach within 5 minute (walk)!brbr- Cape Ann Coffee & Dunkin Donutsbrbr- Shaw's, Market Basket, and Stop and Shop right up the streetbrbr- Charlie's Restaurant (great breakfast and lunch spot), among other restaurantsbrbr- Gloucester Center is only a 1.5 miles away, with great shopping, dining and nightlife!brbr- Rockport is only a 10 minute drive from the homebrbr- Liquor store right up the street, you're on vacation, right !brbr- Long Beach Dairy Maid and Surfside Subs, steps from your front door! Top of the hot summer day with an ice cream, or order sandwiches for the beach!brbr....and so much more!brbrWe would love to have you in our home, please let us know if you have any specific questions about the home or area! Week rentals only (Saturday-Saturday) June-September.

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$427.65

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Private Vacation Home

Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck

Gloucester, Massachusetts, United States

Welcome to Summerwind Cottage! Wake up to harbor views, enjoy coffee or sunset cocktails on a spacious private deck, and walk everywhere from this bright, coastal retreat in the heart of Gloucester.brbrThis thoughtfully furnished two-bedroom home offers a relaxed seaside feel with comfortable living spaces, natural light, and a large deck overlooking the harbor — a guest favorite for dining, lounging, and taking in the view. Located just minutes from downtown Gloucester, you can easily walk to restaurants, shops, galleries, and the waterfront, with beaches only a short drive away.brbrThe home sleeps up to five guests comfortably with two bedrooms and a full sofa bed, making it ideal for couples, friends, or a small family looking for a peaceful coastal getaway. Two off-street parking spaces are included — a rare and valuable amenity in this location.brbrWhether you’re here for summer beach days, fall foliage, arts and culture, or a relaxing coastal escape, this home offers the perfect balance of convenience, comfort, and calm.

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$176.86

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Apartment

Charming Studio, Private Bath, Kitchenette, Deck, Walk to Beach

Gloucester, Massachusetts, United States

Large attractive studio, windows with great winter views, leafy vista In the summer. Firm queen-sized bed. Well-equipped space with desk, large kitchen table, wardrobe. Bathtub/shower in large bathroom, kitchenette and small deck. Owners live on upper floor and are available with tips and suggestions. The quiet street surrounded by trees is a 10 minute walk to Good Harbor Beach. Downtown Gloucester is 1/2m. to 1 m walk with its shops, restaurants, museums, whale watch, boat cruises, fishing charters, and other attractions. In winter, great spot for a getaway with large table for projects. Designated parking spaces.

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$1238.56

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Private Vacation Home

Annisquam Singing Pines: Riverfront Splendor

Gloucester, Massachusetts, United States

Experience a Classic Cape Ann Summer at Annisquam Singing PinesbrbrImagine spending your days swimming from the private dock at high tide or exploring the sandy shoreline at low tide. Launch a kayak or paddleboard from the beach and glide across the water to nearby islands or Wingaersheek Beach for a day of sun, surf, and adventure. Nestled on over an acre of waterfront land, Annisquam Singing Pines is a historic retreat that offers stunning river views, ample outdoor space, and charming indoor comforts—all designed to create unforgettable vacation memories.brbrOriginally built as the summer home of Governor Bates, Massachusetts’ governor at the turn of the 20th century, this beautifully updated home seamlessly blends historic character with modern amenities. With five bedrooms and space for up to 10 guests, this is the perfect destination for family gatherings, friend getaways, or a relaxing waterfront escape.brbrProperty Highlights:brExpansive Waterfront Property – Private dock, beach access, and panoramic viewsbrMultiple Porches & Outdoor Living Spaces – Screened-in and open-air optionsbrRenovated Kitchen (2023) – Fully equipped with modern appliancesbrHistoric Charm Meets Modern Comforts – Updated interiors with original characterbrPrime Location – Easy access to Gloucester, Rockport, Salem, and BostonbrParking – There is off-street parking for up to 6 cars.brbr2,418 SF. No Smoking. No events or parties. No fire pits allowed.

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$909.89

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Private Vacation Home

Salt Island Views: 4-Season Beach House

Gloucester, Massachusetts, United States

Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable ocean-view vacation rental home. Spend the day at the beach where you can swim, soak in the sun, or walk at low tide out to picturesque Salt Island.brbrA ten-minute stroll in the other direction will bring you to Long Beach, often filled with surfers as they catch the waves. An ice cream stand, luncheonette and several roadside eateries are nearby.brbrPrefer to stay at the house Relax and read a book on its expansive deck taking in the views of the sparkling Atlantic with sailboats parading by. Inhale the fresh salt air, and listen to the muffled sound of the waves lapping the shoreline.brbrEnter from the parking area to the home’s lower level. This level includes the entrance area, a spacious queen bedroom, full bath with shower, laundry room and a den. From here you can head outside to the front yard area or up the stairs to the main living space.brbrThe stairs open into a sitting room with comfortable sofas and large picture windows that look out over the expansive deck and the Atlantic Ocean beyond. Walk into the next open plan room with another seating area and a flat screen TV, kitchen with breakfast bar, dining area and more picture windows and sliders leading out to the ocean side deck. This floor has two bedrooms, one a queen and one with two double beds, as well as a full bath with tub and shower.brbrYou are bound to make many happy memories at this wonderful Briar Neck vacation home.brbr1,284 SF. Dogs allowed. No smoking. No events or parties.

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$735.83

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Private Vacation Home

Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive

Gloucester, Massachusetts, United States

Riverdock Cottage was completely renovated in 2017 and has received some new updates for the 2022 rental season, including new Nectar Premier Memory Foam mattresses in the 2 Queen bedrooms, new pillows, new linens and towels.brbrNestled down a private driveway on the waterfront of Lobster Cove, The Cottage boasts a completely renovated interior and exterior with top-quality work, brand new appliances and furnishings and beautiful coastal decor.brbrStarting in the open, white kitchen with its stainless steel LG dishwasher, LG cafe door refrigerator, LG range and microwave, this will be the gathering spot to come together after a long day enjoying the water and local beaches. Enjoy cocktails and apps on a beautiful handmade walnut bar overlooking the step-down eating area and family room and views out to the cove, footbridge and the western sky. brbrThe kitchen comes stocked with brand new cookware, blender, toaster, ceramic dishes, and multiple serving dishes, bowls and platters. Granite counter, center island and tile flooring complete the ambiance.brbrThe first floor full bath, located off the kitchen, is the highlight of the Cottage, with custom tile, rimless shower, free-standing soaking tub and double vanity sink with marble countertops. brbrThere is also a stackable washer and dryer off the kitchen in a closet.brbrThe first floor Master bedroom has it's own access to the bathroom, Queen bed, Wall-to-wall carpeting, full closet and Pottery Barn sea-life comforter. All bedrooms have top-quality sheets and towels - no need to bring your own!brbrThe family room and dining area round out the lower part of the first floor of the Cottage. The family room has original detailing including fireplace (non-working) and built in bookcase and big windows overlooking deck and cove. Flat screen TV above the fireplace, coastal comfy couch and other seating provides a comfortable gathering area to rest after a long day of playing in the great outdoors. There is a handcrafted dining table for 6 and views, views, views.br At high tide, you feel as if you are right on the water. Please note - The house is not wheelchair accessible as there is a step-down to the main living area.brbrThere is a glass french door that leads out to the deck overlooking the water. Table with umbrella and seating for 6 ensures lunches on the deck under the shade of a cedar tree. There is sun on the deck all day long, but once in a while you need some shade from the tree, glad we didn't cut it down! Two lounge chairs sit on the grass below the deck for sunbathing. Beach towels and 6 beach chairs plus umbrella and cooler are included.brbrThe second floor consists of two bedrooms with water views and a half bath. One bedroom has a Queen size bed. Second bedroom has two twin beds . Both bedrooms share the cute half-bath accessed by barn doors. Both rooms have Pottery Barn duvets and top-quality sheets and towels.brbr Maximum accommodations in beds are for 6, any additional guests will incur a extra fee. brbrAs this is an older home built in the 1920's, the ceilings on the second floor are lower than usual, but still able to accommodate someone over 6' tall. The ceilings on the first floor are over 8 feet high.brbrThe Cottage boasts incredible views looking out towards Annisquam Village, Lobster Cove and the river in the distance. Direct waterfront provides access for kayaking, stand-up boarding, swimming and fishing right from the property. An 11-slip dock is part of the property, so accessing the water for the kayaks is easy. The slips are fully rented and the owner has use of two slips and parking. No one else will be parking down at the slips, except the owner. Guests can use the footbridge dock for pick-up and drop-off from small boats. No short-term or overnight dockage is available at either the town footbridge dock or on our dock.brbrRiverdock Cottage is accessed by a private drive off of Washington Street, that appears to be very steep down to the water. However, once you do it, it's easy! Parking for two cars max is available. Owner will also have access to driveway and parking throughout the summer. No one else will be parking at the docks. A privacy hedge separates the driveway from the cottage and the neighbors. brbrAlthough the cottage is private and quite, the waterfront can be quite active on the weekends with lobsterman and their boats, fishing boats, sailboats, little power boats, kayaks, stand up boards and people of all ages enjoying the water. There is always something to look at! You may even catch a wedding on the footbridge.brbrYou won't be disappointed with your stay at Riverdock Cottage. To see reviews on another property I rent out on VRBO, please visit property number 561483 - The Loft at Lane's Cove. I currently have 52, 5 STAR reviews for that property and expect the same reviews for this property. brbr

3

Bed

1

Bath

6

Sleeps

$1203.72

/ Nightly

Private Vacation Home

Gull's Nest - Ocean Views from the Living Room

Gloucester, Massachusetts, United States

Perched on a hill overlooking Ipswich Bay, this inviting coastal retreat offers sweeping views that stretch from Plum Island all the way to New Hampshire. Just a short walk to the sands of private Coffins Beach or the popular Wingaersheek Beach, this home combines seaside tranquility with easy access to two of Gloucester’s most beautiful shores.brbrInside, the main level features bright, open-plan living with a modern kitchen, dining, and living area, all designed to take in the serene ocean views. A full bathroom and two comfortable bedrooms (one with a full bed and one with a queen) make this level perfect for simple, convenient living.brbrStep downstairs to find an additional living area with a shuffleboard table, a spacious bedroom with a king bed and two twins, a bonus sleeping area with a queen bed, a second full bathroom, and even an extra kitchen, ideal for larger groups or families traveling together.brbrOutside, relax on the deck and enjoy the sea breeze and beautiful views of the bay. With 3 bedrooms, 6 total beds, and space to sleep up to 10 guests, this home is perfect for a memorable Cape Ann getaway for families.brbrNo smoking. No events or parties.

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$1446.78

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Private Vacation Home

Niles Beach House - Beach & Boston Skyline Views

Gloucester, Massachusetts, United States

Take in the amazing view of Gloucester Harbor and the Boston skyline from this modern, fully air conditioned vacation rental. Dine al-fresco on the the large deck, or take in the view from the comfortable living and dining room with it's high ceilings, abundant seating and air conditioning. Walk a few steps across the street right onto Niles Beach, perfect for swim during the day or an evening picnic.brbrThe updated kitchen has an electric range, stainless steel appliances and a coffee bar. It opens to the living and dining areas with a couch, high top table, dining table and tv.brbrThe first floor boasts a full bathroom with an exterior door, so you can rinse off from the beach without getting sand in the house, hooks for your beach towels and laundry. Down the hall is a large air conditioned king bedroom with a double closet and sitting area. Across from it is a comfortable twin bedroom with AC.brbrWalk upstairs to a sitting area with a smart tv, small desk and comfy chairs. Enter into the queen bedroom with a stunning ocean view and AC. Across the hall is a room with two queens, AC and water view. It has a door to the shared bathroom which has another door to the hall.brbrNiles Beach House is the perfect family beach getaway with amazing views, easy beach access and all the modern comforts you can ask for.brbrNo pets. No smoking. No events or parties.

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$160.1

/ Nightly

Apartment

Walk to the ocean, very private. Secluded, woodsy location.

Gloucester, Massachusetts, United States

We are a cozy studio in a unique setting. There is a babbling brook that runs through the property to the ocean. This was a granite-quarrying site many years ago, and the property retains the remnants of a granite road used by ox carts to move granite blocks to the schooners. There is wild life on occasion, we recently had a great blue heron for several days. State park on the ocean is a 20 min walk.

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$924.77

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Private Vacation Home

Short Walk to Cape Ann's Best Beaches!

Gloucester, Massachusetts, United States

Come escape to Rockport House, located in Gloucester MA, home of America’s historic fishing town and the best of New England beaches! Our 4BD/2BA,1,850 sq ft house has everything you need—plenty of space to comfortably sleep a group of eight, off-street parking for up to four cars, and brand new furnishings and amenities updated in 2023. The house is conveniently located within a few minutes walking distance to both Long Beach and Good Harbor Beach - no need to think about reserving and paying for beach parking! brbrOur sun-filled split level ranch house, offers an abundance of modern utility and comforts! The front of the house faces west overlooking a large private yard that wraps around to the back of the house. A half flight of stairs up from the front door entrance, you will be welcomed by our open concept living, office, dining, and kitchen layout. The living area includes a six seat sectional sofa, two lounge chairs, 55 inch Smart TV, and stereo sound system with Bluetooth connectivity. Looking for a place to set up your laptop to tie up a few loose ends at work No problem, the main living area includes a small work desk, office chair, LED lamp, and USB plugin capabilities. Enjoy a beverage from the coffee/tea bar, packed with a variety of flavor choices, creamer, and sweetener options, to re-energize after unloading the cars and the long drive. brbrThere is an abundance of amazing restaurants, pubs, and ice cream shops in the area but if you prefer to stay-in and cook, we have you covered. Our kitchen is well equipped with dishwasher, stove/oven, microwave, fridge/freezer and a variety of small cooking appliances such as an Instant Pot, blender, toaster, air fryer. We have plenty of pots and pans, indoor and outdoor serving ware, grill tools, pantry basics, paper products, and cleaning supplies. Choose to dine at our eight seat table, at the kitchen island bar, or on our main level outdoor deck. Our patio dining layout includes a Weber grill, table seating for eight with umbrella, and lounge area with large outdoor sectional and comfy chairs. brbrThe main level of the house includes mini-split air conditioning, and for the super hot days, each bedroom as an additional cooling tower to supplement ceiling fans. All of our bedrooms include pillows, linens, luggage racks, hangers, full length mirrors, USB charging ports, and plenty of closet space. Choose to slumber in one of the four bedrooms with bed sizes: king, queen, queen, and two twins. brbrThe two full bathrooms include bath, hand, and wash towels and toiletries such as shampoo, conditioner, body soap, lotion, q-tips, cotton balls, make-up wipes, and hair ties. Packed light and need to do laundry We have small laundry room equipped with frontload washer and dryer, iron, ironing board, clothes drying rack, and plenty of laundry pods and dryer sheets. brbrThe lower level family/entertainment room is well equipped for indoor fun, loaded with a variety of board games, large sectional and a 55 inch smart TV with a surround sound theater system. Bring your own passwords to stream your favorites or enjoy options on Samsung TV plus our Disney, Hulu, and ESPN+ accounts. brbrCape Ann beaches are a huge attraction for vacationers and tourists visiting New England. Rockport House has you prepared for fun days at the beach (beach chairs, beach wagon, umbrellas, beach towels, cooler, cornhole, kids beach toys). We have an outdoor shower below the upper deck to cool off or wash off beach sand before coming back indoors. At dusk, gather around the fire pit to share beach stories, roast marshmallows, and relax in our Adirondack chairs. brbrEnjoy your stay at Rockport House!brbrGloucester Beachesbr• Long Beach (3-4 minute WALK)br• Good Harbor Beach (8-10 minute WALK)br• Wingaersheek Beach (15 minute drive)br• Half Moon Beach (9 minute drive)br• Plum Cove Beach (13 minute drive)br• Niles Beach (8 minute drive)br• Pavillion Beach (7 minute drive)br• Cressy Beach (9 minute drive)brbrAreas Near Gloucester with Beachesbr• Rockport MA (Front Beach, Back Beach, Long Beach, Old Garden Beach, Pebble Beach, Cape Hedge Beachbr• Ipswich MA (Crane Beach, Pavillion Beach)br• Manchester by the Sea (Singing Beach)brbrGloucester Points of Interestbr• Beauport Hotelbr• Hammond Castle Museumbr• Eastern Point Light Housebr• Fishermen’s Memorial Monumentbr• Stage Fort Parkbr• Main Streetbr• Cape Ann Harbor Toursbr• Cape Ann Whale Watchbr• 7 Seas Whale WatchbrbrbrTransportationbr• Cape Ann Transportation Authority - serves the city of Gloucester and surrounding towns, two stops in West Gloucester and in downtown Gloucesterbr• MBTA Commuter Rail - access to the Newburyport/Rockport Line of the which extends from Rockport along the North Shore to Boston's North Station. br• Boston's Logan International Airport - largest and nearest national and international air service

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$1060.87

/ Nightly

Private Vacation Home

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Gloucester, Massachusetts, United States

This is the vacation house you have been looking for! Perfectly located only a few steps from the world famous Wingaersheek Beach, as well as, your own private access to Coffins beach. The younger crowd will love the excitement of the public part of Wingaersheek beach, while the private access to Coffins Beach is unexcelled for that quiet relaxing time. Why have to make a choice when you can have them both All within a few minutes walk (300 yards) to the white sands of the public side of Wingaersheek beach or less than 2/10 of a mile to the private neighborhood section of the beach called Coffins beach. This immaculate and graciously appointed home is the perfect destination for discerning beach lovers who want only the best in accommodation, sea & surf!br brHousing accommodations are a perfect set-up for the extended family or share with the best friends. This location contains 4000 sq/ft. of housing for your enjoyment. This is one of the biggest houses available in the area. Once you enter the driveway and proceed up to the house you will immediately feel like you are on vacation and ready to enjoy your stay. There are numerous outdoor custom built-in mahogany sitting benches and patios to enjoy the beautiful weather and enjoy the wonderful landscape from the deck swing. As you walk-in the first floor entrance into the spacious custom tiled foyer entrance, you will immediately feel the beach house charm! The rest of the first floor contains an expansive in-law/au-pair suite, which is on your left down a few steps into a very large queen bedroom with a sitting area with TV and cathedral ceilings. You will also find the separate laundry room off the entrance foyer. To your right you will find two more large bedrooms and two custom full-size bathrooms as well. Don’t forget the additional Wifi equipped office space which can be used as a bedroom if needed. The rest of the first floor living room contains a large TV, and a spacious and comfy living room set, and don’t forget you can always challenged each other at the 3-in-1 game table (your choice of pool, ping pong and air hockey) Once you climb the stairs to the second floor you will find the gourmet kitchen featuring a world-class WOLF commercial gas stove. The granite counters, custom cabinets, and oversized chef's gas stove (complete with pot-filling faucet), pantry and stainless appliances completes this home so that it is the perfect place to be the ultimate beach home away from home. Produce your family’s favorite recipes or try some of the great local dining options, its all up to you. Beyond the 8 chair kitchen, you can relax at the kitchen nook by the fireplace, or continue to the formal dining area. The open concept dining room with seating for up to 10 is surrounded on two sides by custom built-in shelving, this in turn leads into the gorgeous Living room where you can view the surroundings from the stunning Palladian windows, surrounding you on all sides. This area doubles as another gathering place to relax with a plush leather sitting area open to the kitchen making it a great space for entertaining as everyone can be together (but still out of the cooks way) in comfort! The king sized master bedroom with cathedral ceilings is located on this floor as well. It contains your own custom full-sized bathroom and another sofa set with a hidden TV, and of course your own large private mahogany deck. The King size bed actually looks small in this space! The house is air conditioned if you prefer, or you can enjoy the sea-breeze air and open the three sets of oversized Anderson sliders. (Five sets if you combine both floors!) Which open onto to the expansive upper mahogany decks, where you can relax on the outside deck furniture and sunbath privately instead of the beach if you prefer The house has wifi, of course, but bring your cell phone as there is no landline at the house. Plenty of parking in the driveway and lovely landscaping outside! Additionally, Gloucester is becoming a more and more artwork-culturally known area; take a ride to the local artwork shops found around Rocky Neck. Find your next treasure to remind you of your stay. There is everything you would expect for a great ocean beach stay, located only 10-15 minutes drive to Gloucester harbor. Once you experience this vacation house and locale, you will want to return for years to come. Start a new tradition and make a reservation today!brbrPlease note: our cancellation policy is if you need to cancel, it is based on our ability to re-rent the booked time, and we always have fulfilled any cancellation.br br...... Exciting news, we are adding a Classic restored 1965 Pontiac GTO or a 1986 Trans Am for rental during visiting guest stays. Enjoy the area even more in a Classic GTO or Trans Am. Please ask about rates and pictures if interested. br

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$265.81

/ Nightly

Apartment

Ocean Breeze / 8-Minute Walk to Beach

Gloucester, Massachusetts, United States

Ground level apartment with one bedroom (1 king bed) and a living room that converts into a second bedroom at night (1 queen sofa-bed). One full bathroom, fully equipped kitchen and free parking space for one car in a shared driveway. Strategically located between the two nicest beaches in the area (Good Harbor Beach and Long Beach) and a short drive to parks, train station and downtown for shopping and dinning. Fully furnished, utilities, Wi-Fi and laundry included. Ideal for up to 4 people. Nice neighborhood, 5-minute drive to Rockport, 20 minutes to Salem and 50 minutes to Boston. I live upstairs with my wife and there may be some ambient noise that travel through the walls (both ways).

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$2664.05

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Private Vacation Home

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Gloucester, Massachusetts, United States

Special corporate meeting day rate for January - March!!br☀ 24 guests across 9 BRbr☀ Perched on the Back Shore ~ 1 mile or 5min drive to Good Harbor Beachbr☀ 22 acres to explore including: formal gardens, cranberry bog, pond, fountain and spacious lawnsbr☀ Ocean views on 2nd and 3rd floorsbr☀ Yoga studio on 2nd floor and gym w/Peloton on 1st floorbr☀ Updated kitchen with butler's kitchen for entertaining br☀ Game room with pool tablebr☀ Large primary suitebr☀ Library stocked with books + gamesbr☀ Hi-Speed WiFi and Smart TVs brbrWelcome to Cranberry Hill, your private estate perched on a hill overlooking East Gloucester's stunning Back Shore. The sprawling 22 acres was designed by Ezra Phillips in 1924 and carefully preserved while updating with modern conveniences. Enjoy grand formal rooms, cozy sunrooms, a spacious entertainment kitchen, and a luxurious primary suite. Conveniently just minutes to Rocky Neck, Bass Rocks Golf Club, and Good Harbor Beach. With almost 9000 sq feet across 3 floors this space is perfect for groups of all sizes to gather or spread out as they wish. brbr5 Min Drive to Good Harborbr5-10 Min Drive to Gloucester's Main Street (Beauport Hotel, Cruiseport, etc)br30 Min Drive to SalembrbrPlenty of space for special events. Please inquire with more details on the type of event you would be interested in hosting so we can give you more details.brbrExperience Cranberry Hill With Us & Learn More Below!brbr☆☆ FIRST IMPRESSION ☆☆brPass through Bass Rocks Golf club and enter the coveted Way Road enclave as you make your way up Cranberry Hill. The long gravel drive provides plenty of parking for multiple cars in front of this private estate. Head into the grand front entrance or choose the side entrance where you'll find a convenient mudroom to return from beach trips.brbr☆☆ KITCHEN, DINING, SUNROOM ☆☆brbrEntering through the side entrance you're immediately greeted by a bright and warm floral wallpaper. To your left you'll find a convenient mudroom/laundry room with plenty of space to kick off shoes and throw beach clothes in the washer and dryer. brbrEnter the light filled eat-in kitchen with comfortable window seat overlooking rolling green lawns. The classic and updated kitchen is well-equipped with stainless steel appliances, a center island, and no shortage of counter space. Two sinks, two dishwashers and a double oven make this the ideal spot for a large group to cook. And if this wasn't enough space, walk over to the large butler's pantry for more room to prep.brbrA warm sunroom provides another space for a group of 6 to enjoy a meal while overlooking the grounds. This leads right into the formal dining room where all 22 guests can gather around the table in this thoughtfully designed space. br br☆☆ LIVING, PATIO, GYM ☆☆brbrThis nice open floor plan leads right into a flexible and elegant living room. Multiple groups can choose to gather in this space: unwind on the sofas by the fireplace, pick up a game of chess at the bistro set, or relax in the comfortable barrel chairs. A smart TV gives the option to sign in and stream any of your favorites together! This well-lit space is tastefully designed with both new furnishings and vintage finds to pull in its historic character. brbrYou'll also be able to connect to an indoor/outdoor sound system to be able to enjoy background tunes wherever you choose to gather! French doors lead you right out onto the brick patio where you can pull up a lounger and rest under the shady awning. This patio is also equipped with 2 outdoor dining tables as well as a gas grill for dining al fresco. brbrA second sunroom also leads out to the patio. This sunroom is furnished as a gym space complete with rogue squat rack, dumbells, and Peloton bike. No need to skip your workout and enjoy beautiful views of the grounds while you do it!brbr☆☆ LIBRARY & GAME ROOM ☆☆brbrRight inside the grand front entrance here you'll find a convenient half bathroom with ornate original wallpaper. As you explore the entry and last wing of this first floor stop to take in unique original artwork in the halls. Enter the library a distinguished space of shelves lined with plenty of books, art, and board games. You'll also find here a record player bringing this space truly back to it's original 1920's roots. brbrOff the library you'll find a full bathroom with fun vintage wallpaper and a full tub and shower. The bathroom also leads out to the game room another sophisticated space that steps back in time with a pool table and leather wingback chair to unwind.brbr☆☆ SECOND FLOOR ☆☆brbrHead up the stairs and you'll find a long hallway lined with 6 of the 9 total bedrooms. All bedrooms are furnished with 100% cotton linens from California Design Den and memory foam mattresses for a truly luxurious night's sleep. The first bedroom Folly Cove is furnished with 2 full beds and surrounded by plenty of windows for natural light. The cranberry walls are a nod to the estate's name and furnishings give a vintage vibe. A large closet and dresser provide plenty of space for suitcases to unpack.brbrThe next room on this floor, Half Moon Beach Studio is a yoga studio for those who want a place to truly retreat. This space is stocked with yoga mats, dumbbells, exercise bands, and mirrors to guide your practice. brbrThe full bathroom on this wing is a newly tiled space with bathtub and shower. Each bathroom is equipped with hair dryer and bath amenities (shampoo, conditioner, body wash). Our housekeeping staff provides a fresh set of towels on each bed.brbrThe next bedroom pulls from Good Harbor Beach just down the road. This cozy nautical space is furnished with a bunkbed with 2 full sized mattresses. A dresser with mirror also provides a place to unpack and get ready. brbrPlum Cove is the next bedroom and the most spacious thus far. This space is fitted with a comfortable King bed as well as a desk set up with 2 monitors for a robust workspace. There are multiple closets with built in drawers to unpack and a full length mirror for getting ready. A decorative fireplace, ocean views, and dramatic red accent wall make this an unforgettable suite. This room also has an en-suite bathroom truly making it like a second primary suite. Step down into the newly tiled bathroom and you'll find a tub and shower along with traditional fixtures like pedestal sink and sconces. brbrPavilion Beach Lounge is a flexible room conveniently located in the middle of both wings. This vibrant green space provides another space to gather while also serving as an additional bedroom as the comfortable sofa pulls out to a queen bed. A stunning antique hutch from the 1600's houses a smart TV for guests to sit back and enjoy a movie night. brbrThis room has an en-suite vintage style full bathroom with separate stand up shower stall and tub. Another bedroom is also adjacent to this bathroom in a jack and jill style. The Long Beach Bedroom is fitted with a spacious King bed and serene coastal blues, greens, and rattan throughout. A nook with desk offers another remote workspace for the guest on workcation. Closets are equipped with drawers and full length mirror so plenty of space to unpack and make yourself at home.brbr☆☆ PRIMARY SUITE ☆☆brbrThe primary Wingaersheek Beach Suite has a wing of it's own with plenty of space for a bridal party or other events where guests would like to spread out and get ready. There are essentially 2 full bathrooms in his and hers style within this suite. The first bathroom has a large built in closet, vanity, steam shower, and bidet. Adjoining this is another bathroom with toilet, vanity, and shower/tub combo. brbrEnter into the light and bright bedroom and you'll find large 4 poster plush king bed. This luxurious bedroom is furnished with a vanity to get ready, a dresser, and comfortable window seat. Step into the en-suite sitting room and you will be awestruck by the panoramic views of the surrounding grounds. A comfortable sectional and Smart TV make this room an exclusive retreat.brbr☆☆ THIRD FLOOR ☆☆brbrOn the third floor you'll find 3 more spacious bedrooms for guests to claim as their own! A full bathroom is on this floor making it perfect for a full family to have a floor to themselves. brbrNiles Beach Bedroom is a beautifully wallpapered space furnished with a comfortable king bed and with a desk for remote work. Inside the closet you'll find space to hang and unpack in the dresser. Don't miss the stunning ocean views outside your window and serene ocean scenes in the art as well. brbrThe next 2 bedrooms on this floor are Jack and Jill style connected by a full bathroom. Cressy's Beach is another King bedroom with dramatic accent wall and four poster bed. Plenty of space in the dresser or large closet to unpack. The adjoining bathroom has a shower/tub combination and unique vintage fixtures fitting for the time period of the home. brbrThe final bedroom is not to be missed! Breakwater room is set to a beautiful deep sea green with original wallpaper kept on the ceiling. 2 twin beds make this a great space for kids or comfortable enough for 2 adults. Nautical accents like hanging oars and lighthouse lamps create a fun eclectic space here. A sitting nook in the corner makes this the perfect little escape!brbr☆☆ GROUNDS ☆☆brbrAs if there wasn't enough room in this almost 9000 sq ft estate there are 22 acres of grounds to explore outside! Leisurely stroll through the stunning formal gardens enjoying the springtime wisteria and natural cranberry bog. You'll have your own large private pond with bridge and fine impressive granite moraines. The property also boasts a handsome barn, multiple paddocks, and a chicken house. Not to be missed is a private trail with direct access from the property to Gloucester's stunning waterfront.brbr★☆ Book Today & Let Us Take Care Of You at Cranberry Hill! ☆★ brbrYou'll have access to the entire property and grounds except the garage. brPlease remember that you're staying in a house, not a hotel.

9

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7

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24

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