Vacation Rentals By Owner In Gloucester, MA

Incredible wrap around, direct ocean views and walkable to Good Harbor Beach! Beautifully appointed and maintained unit. Fall in love like all of our guests who say it best! What a Dream.vacation ...We loved easy access to beach and the incredible views. ....Awesome! Views are stunning...location is perfect... Loved the short stroll to Good Harbor Beach....Spectacular accommodations....Met all expectations in all ways. Loved everything....amenities provided...sound of the waves. Beautiful inside and out. Walk to Good Harbor Beach recently named one of the top 5 beaches by Travel and Leisure . Or simply enjoy the views and sound of the waves and the coastal beauty unique to our unit. Open floor plan with panoramic wrap around, dramatic, direct ocean views! Beautiful coastal decor with recent updates and amenities meld high end luxury with welcoming comfort. Two large decks - one ocean front facing and one rear facing overlooking renowned Bass Rocks Golf Course. Fully equipped Chef's Kitchen with convection oven, wine and beer fridge, built in bar and microwave, farmer's sink and quartz counters with wide breakfast bar that opens to beautifully appointed DR and LR with deck and large bay window with cozy built in nook to enjoy the sweeping ocean views or just relax with a book. Den with games, books and cable tv offers another relaxing space and opens to second large deck facing renowned Bass Rocks Country Club. Fenced backyard with dining table, chairs, picnic bench & gas grill. Large bedrooms including private, penthouse primary suite on top floor with incredible ocean views, electric fireplace and high end bath . Cable, high speed internet, ceiling fans, a/c. Full laundry room. Due to stairs and decor, please pay close attention and be responsible to any young children.There are strict rules regarding running, jumping and playing outdoor games indoors to help protect your children and are strictly enforced. The back yard is grassed and fenced for outdoor play. Professionally landscaped. Enjoy reading or just some quiet time in front yard listening to the waves and watching the ocean. seating Or enjoy backyard games and dining in your private, fenced back yard with large gas grill, lighting , picnic table, additional table and seating, and outdoor games to enjoy. Rainy day No worries! We have stocked books, puzzles, magazines, and board and card games for your enjoyment. Please note that number of over night guests and cars is strictly enforced and that unit is on the top 2 floors. Additional 1BR unit on first floor, also front facing, may be rented with top floor for additional cost. Located less than an hour away by car or commuter rail from Boston, most major highways and Logan Airport. Book now to ensure your dream coastal vacation, work from home stay, corporate stay (ideal for motivation seminars, company meetings etc) relaxation & rejuvenation stay, special occasion or any reason to experience and enjoy coastal living at its best! Come and experience all that Gloucester has to offer and make a lifetime of memories.

Coastal Oasis with Unobstructed, Direct Ocean Views!

Gloucester, Massachusetts, United States

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Bath

Sleeps

$468.83

Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this cheerful two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway!brbrBoth the living room and the primary bedroom have sliding doors that open onto a spacious, private, sun-kissed deck complete with gorgeous water views, a lounge chair and a table and chairs for al fresco dining, all overlooking the verdant backyard.brbrBoth bedrooms have a queen-sized bed. A well-equipped galley kitchen, pleasant full bathroom with tub and shower complete the unit. Outdoors, one can enjoy the large yard, rife with plentiful herbs and flowers.brbrConveniently located a very short walking distance away from Good Harbor Beach and scenic Bass Rocks, a short drive away from restaurants, stores, a laundromat, and with easy access to Route 128, Garden by the Sea is one the best vacation spots around.brbrPlease note that the friendly owners live in a separate unit of the house.

Garden by the Sea: Walk to Good Harbor Beach

Gloucester, Massachusetts, United States

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Bath

Sleeps

$615.52

KEY FEATURES:br* 2 story townhouse that sleeps 8 comfortablybr* Walking distance to beaches and Downtown Gloucesterbr*Fully equipped kitchenbr*Ocean facing front porch with rocking chairsbr*Hi-speed WiFibr*Keurig coffee maker with complimentary kcupsbr*Off street parking spotbr*Multiple Smart TVsbr*3 bedrooms/2 full bathroomsbr*Pull out sofa for additional guestsbr*Beach gear, bocce set, and tennis rackets brbrLearn more below about this Gloucester Getaway! brbr☆☆ Within walking distance to many of Gloucester's attractions and beaches: ☆☆br2 minute walk to Stage Fort Park and Half Moon Beachbr1 mile from the commuter rail to Bostonbr1 mile to historic Downtown Gloucesterbrbr☆☆FIRST FLOOR☆☆brPull up to this cozy townhouse and park in your private off-street parking space. Step inside and you’re welcomed by a cozy living room space on your left with plenty of seating. The living room is complete with a Smart TV and boasts lots of natural light. Board games provided for cozy nights in. Make your way into the full kitchen, with all the amenities and appliances you need for a home cooked meal. A dining room with a large table with space for 8 is located right off of the kitchen. brbr☆☆SECOND FLOOR☆☆brMake your way up to the second floor, where you will find the 3 bedrooms. The primary queen bedroom has direct ocean views and features an en suite full bathroom with standup shower. There's a smart TV, plenty of space to unpack in the closets and dresser, and a nook with mirror for getting ready. The second bedroom features a queen bed, a closet and dresser, and a desk to get some work done. The final bedroom is perfect for kids. It has a twin bunk bed, a cute reading nook with shelf stocked with books and some toys for kids. Also on this floor is a second full bathroom with a tub. br br☆☆OUTDOOR SPACE☆☆brThis home features a lovely front porch with rockers that face the ocean, a picturesque spot for your morning cup of coffee! Behind the house off the kitchen is a deck with dining table for 4. brbrEnjoy being directly across from the ocean and tennis and bocce courts! The home includes tennis rackets, bocce set, and beach gear. Stage Fort Park is also across the street featuring beautiful Half Moon beach, playground, and plenty of picnic spots.brbrBook today and let us take care of you at this Gloucester Getaway! brbrYou'll have access to the townhouse, front porch and deck.brPlease remember that you're staying in a house, not a hotel.brPlease treat the space with respect. If any problems arise, we will do our best to take action ASAP. brbrI am here for you during your stay, but our level of interaction is up to you. I'm only a phone call/message away. brbr• Check-in is anytime after 4:00 PMbr• Check-out is 11:00 AM or earlierbr• No early check-in or late check outbr• Quiet hours is from 10:00 PM to 8:00 AM

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester, Massachusetts, United States

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Bath

8

Sleeps

Select Dates for Price

Welcome to your ideal seasonal destination! Located just a few steps from not one, but TWO gorgeous Massachusetts beaches, enjoy this spacious private single family home with amenities throughout. Offering three private bedrooms with queen or king beds as well as a loft and living room offering sleeping set ups, this property is a great fit for groups of all sizes. Equipped with a full kitchen offering island seating, a dining room, living room, private office space, and a back yard/ large deck, there is plenty of space throughout the property to relax and enjoy your vacation rental. brNew England Fall is a wonderful stay. We have wedding parties, Fishing trip surf casters, Leaf Peepers heading up North and the glorious Halloween celebration in renowned Salem, Ma. You are a short train ride away from the historic towns of Salem & Boston as well as the beautiful NH/Maine woods with all of the fall seasons breathtaking color.brbrIncluded in your rental are linens for all bedding as well as towels for your stay, along with other necessities to make your stay as comfortable as possible. WIFI, Washer/Dryer, Dishwasher, full cookware & dishes, and smart TVs are some of the other features you'll find inside. Outside and in-season, beach chairs, boogie boards and other beach needs are also provided. brbrA two story unit, you will find the kitchen, living room, dining room and two of the bedrooms/ one bathroom on the main level. Upstairs, the master bedroom/bathroom, loft, office space, and laundry station can be found. Deck is off the main level. The grounds also includes space for 3+ cars comfortably, with room available for others as needed. Speak with the owner for best way to arrange! brbrAside from the accommodations provided on-site, the property is a short walk to both Good Harbor and Long Beach beaches. Pro tip - stop by Surfside Subs on your way back from Good Harbor for the best ice cream! Additionally, a short drive to the historic & quintessential towns of Rockport and Gloucester inclusive of activities for the whole family! Some recommended activities include whale watching, sailing, fishing and checking out a lot of wonderful restaurants and shops.brbrWe are also open for short term rentals through Thanksgiving and Christmas for family gatherings. DO you need extra room for visiting family members - this is the PERFECT place!brAdditionally, we offer 30 day minimum stays available from Jan - April.brbrIt's our hope you will love this home and your experience here the way we have from the beginning! brbr** NOTE: There is a basement studio apartment occasionally rented that shares nothing with the VRBO guests except driveway access to a garage. Yard, deck, porch, patio, parking etc are all VRBO guest use only. We just ask that you do not block the garage door.

Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

Gloucester, Massachusetts, United States

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Bath

Sleeps

$517.05

Summary:brbrYou and your family cannot beat this amazing Gloucester location, walking distance to the best beach in all of New England, Good Harbor. This family home was recently renovated from top to bottom and is awaiting your next stay.brbrbrbrThe Space:brbrYour home away from home has everything you need to enjoy your next North Shore vacation, with views of Good Harbor the location cannot be beat. Only a quick 10 minutes walk to the sand. brbrbrbrRedesigned and recently rebuilt, the kitchen ticks all the boxes for home cooked meals. Bright & open it features: a stove with electric cooktop, dishwasher, garbage disposal, microwave and island with seating for two.brbrbrbrThe kitchen is open to the dining nook which has seating for six. brbrbrbrThe kitchen is stocked with all the cooking/serving necessities including: cookware, pots, pans, plates, cups, and silverware.brbrbrbrComfy living room with multiple seating options. The TV, although it doesn’t have cable TV, it is a smart tv, connected to a RoKu so you can connect to your streaming apps. brbrbrbrThere is a four season sunroom that is a perfect spot for reading or enjoying a cup of coffee. The sunroom opens to the deck and has peaks of the ocean.brbrbrbrOutdoors: Sit on the deck and enjoy ocean breezes, there is also a gas grill outside for cooking up dinner after a day at the beach. brbrbrbrUp one flight of stairs there are three bedrooms all furnished with comfy memory foam mattresses: brbrBedroom 1 & 2: each have queen size bedsbrbrBedroom 3: has a twin trundle, set up as one twin bed but can pull out to become two twins. brbrbrbrHotel quality linens and towels, shampoo, conditioner, and Dove body wash provided for guests. brbrbrbrThere are two bathrooms at the house:brbr-On the first level there is a full bathroom with shower brbr-On the second floor there is a full bathroom with a stunning clawfoot tub. The tub does not have a shower attachment so it is simply a tub to enjoy and relax. brbrbrbrOther amenities worth noting: brbr-The house has only been owned by two families and has been used by the current owners for generations. Beginning in mid 2020, they gutted the house to the studs, reconfigured and rebuilt it. Most of the furniture came back to the space to blend the new construction with their family history. brbr-The backyard overlooks the marsh which then overlooks Good Harbor Beach. There are so many colorful birds in the back yard that bird watchers may confuse the backyard with a bird sanctuary. brbr-Only two steps to the front door, 12 stairs to the 2nd floor brbr-Washer/dryer available for usebrbr-Small parking area with space for two cars tandem brbr-Fast wifi throughout the house brbr-Gas heat to keep you warm in the winter.brbr-There is a large floor AC unit on the first floor to keep the main living area cool. Upstairs there is one window ac unit. The rest of the house gets great cross breeze while the windows are open.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.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:brbrAll guests to agree to our rental agreement within 24 hours of booking.brbrbrbrThe owners of the house have lovingly furnished the home for you to enjoy. They ask in return that you respect their privacy by following the following rental agreement:brbr-No parties, partying, general rowdiness or events. Fines assessed for additional cleaning, trash removal and property damage. A party is grounds for termination of stay and immediate removal with no refund. brbr-Smoking is strictly prohibited both inside and within 50ft of the outside. After 8PM, smoking should be done individually to keep noise down. brbr-No sublet, and no packages may be sent to the apartment without host approval.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.brbr-No pets are allowed. brbrbrbrIf you are booking through VRBO: You agree that The Host will charge your card for the full payment of the stay 24 hours after booking. Any payments by VRBO (service fees) will be charged separately.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.

Walk To Good Harbor, OCEAN VIEWS, Open All Year!

Gloucester, Massachusetts, United States

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Bath

Sleeps

$377.49

We've curated the perfect North Shore experience for you. Enjoy the vibrant fishing port of Gloucester, the rich history of Salem, the elegant shores of Manchester by the Sea & Beverly, and the antique charm of Essex, all from your stay at The Essex of Gloucester.brNestled on the Gloucester/Essex line, this pleasant house offers a cozy retreat for guests. With two comfortable bedrooms featuring queen beds, it’s perfect for a small group or family. The single bathroom includes a hair dryer for added convenience. Guests enjoy a well-equipped space with heating and air conditioning to keep the atmosphere just right. Whether relaxing indoors or exploring nearby, this gorgeous home provides a welcoming base. Experience what Gloucester has to offer with a stay at our house.

The Essex of Gloucester

Gloucester, Massachusetts, United States

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Bath

Sleeps

$478.45

This property is a 650 sq. foot cozy cottage on Ipswich Bay with unbeatable views facing west, making for beautiful sunsets over the bay. Perfect for a couple or small family, there is a king bedroom, and a twin bedroom. There is a large deck overlooking the bay with an outdoor shower with amazing views, and a back patio with a Weber grill and a hammock, also great views. The cottage is an easy 5 minute walk to a neighborhood beach nearby.. Please be aware that this is an old cottage. It is not wheelchair accessible, and has different levels within the house. Also please be aware that this is a private home owned by my elderly mother who uses the property regularly. She is extremely allergic to animals, where reactions are extreme and debilitating at her age. Please understand the house is not suitable for a service or emotional support animal. Thanks for your understanding.

Cottage

Bayview Guest Cottage

Gloucester, Massachusetts, United States

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1

Bath

Sleeps

$1010.83

Right on the canal where ships and boats pass by all day, and just a hundred yards to see the great ocean view on Stacey Boulevard, home to the Fisherman’s memorial and Fishermen’s Wives memorial, as well as the beautiful gardens that stretch on the way to Stage Fort Park. Close proximity to restaurants and the old part of the town.brThe house is composed of two full apartments that can be opened for passage between. Perfect for extended families that want their own space while still sharing.brWe are delighted to be pet-friendly, but please keep your pet on the first floor. We provide water and food bowls to make your furry friend feel at home. For a wonderful outing, we recommend taking a stroll down the scenic boulevard to Stage Fort Park, where you'll find a fantastic dog park perfect for your pet to enjoy.

Waterway View; Steps to Ocean, Beach, Blvd, Park

Gloucester, Massachusetts, United States

4

Bed

Bath

9

Sleeps

$643.07

Located in the Lanesville section of Gloucester, nestled just above Plum Cove Beach which beckons from the kitchen window, this house is a marvelous retreat for any family or anyone seeking a wonderful experience. Walk on your own path to Plum Cove beach . It is perfect for anyone, especially families With young kids. It is known as Mothers beach due to the coves perfect shape and sand. With 3 cozy bedrooms, including 2 BRs with queen beds, and 1BR with 2 twin beds as a Trundle bed, you'll find the perfect spot to unwind after a day of exploration. The bathroom offers a refreshing shower and also an outdoor shower to wash the sand off. Amenities like AC, grill, kayaks, large deck with an awning to ensure shade and keep you out of any rain as you enjoy the serenity of birds chirping, THE SUNSETS and the silence of this piece of heaven. , washing machine,, AC, heating, WiFi, and iron ensure a phenomenal stay. Whether you're relaxing in the comfortable living spaces or venturing out to discover the local gems, this charming house provides everything you need for a memorable getaway. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out. Also highly recommend a sail on The Artemis Captained by Rick Miles. It is a gorgeous yacht!

Plum Cove Beach Paradise. Overlook Plum Cove from your kitchen n only steps away

Gloucester, Massachusetts, United States

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Bath

Sleeps

$297.53

Your cozy getaway awaits in Gloucester at this charming apartment. With 2 bedrooms, including a king bed and a queen bed, it's the perfect retreat for guests. The bathroom is equipped with a hair dryer and a bathtub for your convenience. In addition to the comfortable bedrooms, there is also a living room with a sofa bed, providing additional space for relaxation. AC, WiFi, heating, a washing machine, and an iron are among the amenities available. Enjoy all that Gloucester has to offer when you stay at our place.

Blue Magnolia - A quiet apartment in a quaint Gloucester MA village

Gloucester, Massachusetts, United States

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Bath

Sleeps

$608.96

Two-bedroom gorgeous beach house overlooking Good Harbor Beach, located DIRECTLY on the Good Harbor estuary. The house is a 4-minute walk to the beach where you can enjoy everything New England's top-rated beach has to offer, without dealing with parking, crowds, or traffic. Amenities include a private patio, off-street parking, an outdoor shower, a gas grill, and a gas wood stove.brbrThe space:br@thehaabah / #thehaabahbrbrA truly unique Cape Ann home, The Haabah is as perfect for a couple craving a retreat, a family on a beach getaway, or can comfortably accommodate a family or friend group of up to six.brbrPark in two dedicated off-street parking spaces and you're less than a 4-minute walk to the ocean. Our beach house has the creature comforts of a hotel, but with a magnitude of more soul.brbrAn open-concept kitchen/living area greets your arrival. Stainless steel appliances, granite countertops, and a full range of kitchen appliances. Gas woodstove resides in the living room for those chilly mornings or beautiful sunset evenings.brbrOur beach house is equipped with a beautiful marble eat-in kitchen with a breakfast bar, as well as a dining table that seats 6 adults. Complimentary coffee from our friends at Little Wolf coffee, as well as a full-size Cuisinart coffee maker, and accouterments for pour-overs. For cooking, a natural gas range and oven, Cuisinart toaster oven, Henkel chefs knives, and Caphalon non-stick pans. Also have everything you might need for beer, wine, and cocktails (juicers, shakers, jiggers).brbrFor sleeping, we've outfitted the space with two queen-sized beds, as well as a brand-new Joybird sleeper sofa. 3 brand new high-efficiency GE window AC units.brbrOutside, you'll find a heated outdoor shower, a privately lit patio, and a Webber gas grill. The patio is a perfect place to watch daybreak over the marsh with your morning coffee, and the nearby grill for fresh lobster or the day's haddock, watching dusk with your beverage of choice.brbrLastly, the house has private high-speed Wi-Fi, Xfinity cable, Samsung smart TV, Chromecast, etc.brbrGuest access:brWhile you’re staying with us, you have access to all areas of the beach house with the exception of the several cabinets marked private. Feel free to explore the yard, hang out on the back patio or play a friendly yard game--we have horseshoes, frisbees, cornhole, and mollky.brbrOther things to note:brWe have painstakingly gone out of our way to find antiques, family heirlooms, and unique items that many of our guests admire and enjoy. We only ask that all guests be mindful and respectful of the space (using coasters, using care); unfortunately, any damage or excessive mess will need to be accounted for from the security deposit.brbrTowards these ends, we also ask that at least one member of the party be at least 25 years old.

The Haabah Beach Retreat—4 Minute Walk to Beach

Gloucester, Massachusetts, United States

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1

Bath

6

Sleeps

$301.61

Cozy Harbor View 2-bedroom, 1-bath apartment in downtown Gloucester with deck views of the Inner Harbor and the grounds of St. Peter’s Fiesta. Enjoy ocean breezes, harbor activity, and the charm of Gloucester in every season. Walk minutes to Pavilion Beach and the waterfront. The elegant Beauport Hotel Gloucester is a short 4minute walk for dining and ocean views, with shops and restaurants steps away. Perfect year-round North Shore living.

Harbor View Apartment located in the heart of downtown Gloucester

Gloucester, Massachusetts, United States

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Bath

Sleeps

$1150.51

Luxury is located in a private residential area called Eastern Point, with remnants of an old fort. This modernized 1886 Captain's Carriage House was built with 20-inch stonewalls. Wildlife and water abound. brbrAmazing walks and about a 2 min walk to a private beach, lighthouse, breakwater, and yacht club. brbrYou may want to stroll or snow-shoe through the Audubon wildlife sanctuary, a favorite spot for birdwatchers. Wander through meandering paths to different spots along the sea or harbor. Say hello to the seals sunning at Braces CovebrbrBeautiful sunsets are enjoyed on a magnificent stone patio and terraced firepit area. Turn off the patio stone wall lights and star-gaze with only a roaring firepit for illumination.brbrAll modern amenities are available in this smart home. There are three official bedrooms and a 33x11-foot finished attic. Other sleeping arrangements are available.brbrBlack-out blinds are great for a good night's sleep. Full outdoor kitchen in addition to a modern indoor kitchen with all new appliances, including a double oven for baking wonderful bread. brbrGreat restaurants are a short 5 min ride away to the nearly 400-year-old town of Gloucester (circa 1623) with eclectic choices from Wicked Tuna, Lobtsa, Haddock or clam chowder, or modern American cuisine.brbrThere are interesting museums nearby. One located on Eastern Point The Beauport is a favorite. Hammond Castle is amazing! brbrYou might enjoy a picnic on the harbor at Stage Fort Park, the site of the early 1600s defense of Gloucester. A visit to the memorial to those lost at sea The Man at the Wheel is a sobering tribute.brbrIf it's summer: The St. Peter's Festival with its blessing of the fleet, seine boat races, and Greasy Pole contest is fun for all ages. brGo whale watching or deep-sea fishing!brbrIf you want a hike a short ride to the beautiful woods of Ravenswood Park is there to enjoy. Let's not forget long walks, surfing, or even swimming at one of the most breathtaking topographical beaches anywhere, called Good Harbor. You can walk there in 20 minutes(3 miles) along Atlantic Avenue watching the angry sea crashing onto spectacular Bass Rocks.

Cottage

1886 Captains Carriage House Secluded Luxury Eastern Point Gloucester MA

Gloucester, Massachusetts, United States

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Bath

Sleeps

$737.22

Be our guests at Twin Shores Poolside Haven! brbrEscape to this charming 3-bedroom, 2-bath home that comfortably sleeps 8, offering the perfect blend of relaxation and coastal adventure. Nestled just a 5-minute stroll away from the pristine shores of Good Harbor Beach, this vacation rental promises sun-soaked days and tranquil evenings by the pool.brbrLocation, Location, Location: Unwind in this idyllic coastal haven, mere minutes from the sandy shores of Good Harbor Beach. Short drives to downtown Gloucester and Rockport where you will find opportunities for seaside excursions and a variety of dining and cultural experiences.brbrSpacious Accommodations: With 3 bedrooms and 2 baths, this home provides ample space for families and groups of friends. Relax in comfort and style after a day of seaside fun.brbrPrivate Pool: Take a refreshing dip in your very own private pool, the perfect spot for cooling off or soaking up the sun's rays.brbrFully Equipped Kitchen: Whip up delicious meals and snacks in the modern kitchen, complete with all the essentials for your culinary adventures.brbrEntertainment Options: Wind down in the evenings with a movie night in the cozy living room, equipped with a flat-screen TV and plenty of seating for everyone.brbrOutdoor Oasis: Sip your morning coffee or enjoy evening cocktails on the spacious deck and patio areas, surrounded by lush greenery.Convenient brbrParking: Park up to 3 cars with ease in the driveway, ensuring hassle-free access to your home away from home.brbrWhether you're seeking seaside relaxation, aquatic adventures, or simply a peaceful retreat by the pool, Twin Shores Poolside Haven House has it all. Be the first to book your stay for the season and start making unforgettable memories on the beautiful shores of Gloucester, MA!

POOL OPEN WK OF MAY 17, 2026! Single family home 5min walk to Good Harbor Beach!

Gloucester, Massachusetts, United States

Bed

Bath

8

Sleeps

$1172.85

Escape to this wonderful beach house in picturesque Gloucester just a 2 minute walk from beautiful Coffins Beach (private side of Wingaersheek Beach). Enjoy 3 spacious decks, a large yard for kids to play, and plenty of on-site parking. With four cozy bedrooms featuring a king bed, two queen beds, and two twin beds, guests will find plenty of space to relax. A short drive brings you to downtown Gloucester's shops, restaurants, and harbor attractions. Come make lasting memories at one of New England's hidden gems- known for its wide sandy beach, calm waters, and breathtaking sunsets.

Perfect 4-bedroom beach house second row on private beach

Gloucester, Massachusetts, United States

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Bath

Sleeps

$208.53

Beautiful cottage by the sea in Folly Cove! brCome and enjoy a relaxing retreat style experience in the historically significant area neighborhood of Lanesville, in Gloucester, Massachusetts on beautiful Cape Ann. This cozy, pretty, 646 sq ft cottage offers a studio-style layout, with a spacious sleeping loft upstairs with skylights (and pitched roof) which includes a comfortable queen bed and twin futon. along with a double futon bed in the main living room downstairs. Perfect for 1-2 people seeking quiet and R&R, minutes by foot from the rocky shores of stunning Folly Cove, where you can swim in the cool Atlantic Ocean straight from the shoreline. Cape Ann offers plenty of historical exploration opportunities, from the hiking trails of Dogtown and Halibut Point, to art galleries in Rockport and Rocky Neck, to beach experiences at Good Harbor Beach or Front and Back Beach, to name a few. brbrThe cottage has a small kitchenette that includes a full-size fridge, a microwave and two burner stove with a sitting area for two, and a lovely, well-appointed bathroom with shower. Located on a beautifully landscaped property adjacent to lush woods, the cottage also has a private deck (11' x 9) with gas grill and a one-car parking space. Note: ceiling height 6'8 on main floor, 6'1 at peak in sleeping loft.brbrThere are many excellent restaurants to choose from on Cape Ann, with Italian and fresh seafood being the local specialty. The Lobster Pool, overlooking Ipswich Bay, is a favorite local summer place for fried fresh seafood and hot boiled lobster and lobster rolls within walking distance from the cottage. Come and enjoy all that Cape Ann has to offer from the beautiful cottage by the sea. brbrWe have a 24 hour window to accept bookings. Please submit a message with your request so we can learn a bit about you and what brings you to Cape Ann! We want to ensure our cottage is a great fit for you so please don't hesitate ask for more details about the space, the amenities or location. We look forward to hosting you!

Cottage

Beautiful cottage on lovingly landscaped property just minutes from the ocean!

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1521.49

Summary:brbr✓ 2-Min Walk – Steps from the renowned Good Harbor Beachbrbr✓ Expansive Home – 1 King • 2 Queens • 2 Fulls • 5 Twinsbrbr✓ Chef’s Kitchen – High-end appliances for culinary enthusiastsbrbr✓ Ocean Views – Deck, porch & most bedrooms overlook the waterbrbrbrbrIdeal for families and groups, this spacious home offers the perfect blend of beachside fun and coastal charm.brbrbrbrVisit @stay_collections on IG for a video property tour!brbrbrbrThe Space:brbr☆☆☆ FIRST FLOOR ☆☆☆brbrbrbr→ Living Room: Smart TV + sectional couch for relaxing nights inbrbr→ Dining Area: Large table + kitchen island seating, ideal for family mealsbrbr→ Chef’s Kitchen: Fully equipped with high-end appliancesbrbr→ Laundry Area: Convenient first-floor accessbrbr→ Bathroom: Full bath with modern showerbrbr→ Deck: Water views & ample space for outdoor diningbrbr→ Covered Porch: Multiple seating areas for morning coffee or readingbrbrbrbr☆☆☆ 2ND & 3RD FLOORS ☆☆☆brbrbrbr→ Primary Suite: King bed • Renovated en-suite bath • Stunning water viewsbrbr→ Bedroom #2: Queen bed • Crib • Water viewsbrbr→ Bedroom #3: Queen bed • Water viewsbrbr→ Bedroom #4: Two full bedsbrbr→ Bunk Room: Sleeps 5 in twin beds • Desk & chair for added conveniencebrbr→ Bathroom: Full bath with modern finishesbrbrbrbr☆☆☆ OUTDOOR SPACE ☆☆☆brbrbrbr→ Deck: Ocean views with lounge & dining seatingbrbr→ Porch & Landscaping: Private, peaceful setting with lush surroundingsbrbr→ Grill Area: Conveniently located at the back of the housebrbr→ Outdoor Shower: Perfect after the beachbrbr→ Parking: Driveway fits up to 4 vehiclesbrbrbrbr☆☆☆ BOOK YOUR STAY ☆☆☆brbrbrbrEscape to our expansive waterfront home with breathtaking ocean views, just a 2-minute walk to Good Harbor Beach! Perfect for families, this 5-bedroom retreat comfortably sleeps your group. Enjoy a fully equipped kitchen, central AC, a large deck for seaside dining, and high-speed WiFi. Explore historic Gloucester, just a short drive away. Your ultimate coastal getaway awaits!brbrbrbrGuest Access:brbrGuests will have access to the entire home with the exception of two closets, the basement and the garage.brbrbrbrPlease note: The entrance to the house is via the deck, which is accessed via a full set of stairs as shown in the listing photos.brbrbrbrThe Neighborhood:brbrGood Harbor Beach, just a two minute walk from our home, offers pristine sands and surf plus proximity to a variety of attractions in Gloucester. During low tide, venture out to Salt Island, just offshore to Good Harbor Beach by a sandbar. Local legends say that it once served as a hiding spot for pirates. Just a short drive from Good Harbor, Stage Fort Park offers a historic setting with two beaches, a playground, picnic areas, and a dog park. For art lovers, Rocky Neck Art Colony is a must-visit, featuring galleries, local artists, and charming waterfront cafés. Alternatively, explore downtown Gloucester, where you’ll find a blend of cultural, historical, and culinary experiences.brbrbrbrOther Things to Note:brbrOnce a booking is confirmed, the following cancellation policy will immediately be in effect. Due to automatic platform processing fees, full refunds cannot be issued for same-day cancellations. Cancellations made more than 30 days before check-in are eligible for a 50% refund. Cancellations made within 30 days of the check-in date are non-refundable. No-shows are not eligible for any refund.brbrbrbrInteraction with Guests:brbrWe are here to help, please do not hesitate to reach out! We’re available 24/7 via phone, email, or the booking platform’s app.

Stay at Good Harbor Beach

Gloucester, Massachusetts, United States

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Bath

Sleeps

$694.76

Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the perfect vacation spot. The bright and airy ground floor has many windows, letting in lots of natural light. Upstairs, there are 3 bedrooms and a full bath with claw foot tub and shower. AC units are in each of the bedrooms and the living room.br brTake a walk back in history by strolling through the prototypical colonial village with its white clapboard and black shuttered homes and picturesque lanes that were created to accommodate horse-drawn carriages. This is what you come to New England for -- history on the water! Meander through hidden paths to Lobster Cove where you can swim, kayak or stroll along the scenic water ways. Choose from two sandy beaches in the village or take a short drive to the beaches of either Gloucester or Rockport.brbrGROUND FLOORbr brLiving Room: A sunny room with large windows, a wall-mounted flat-screen tv, and a ceiling fan. br brKitchen: New appliances, including a gas range.br brDining Room: Formal dining room with a drop-leaf table and ceiling fan. br brSun Room: A generous room, running the length of the house, with one Single bed and one Full bed. br br Full Bathroom 1: Main floor full bath with shower. br br SECOND FLOORbr br Bedroom 1: Master bedroom with Queen bed.br br Bedroom 2: This room contains a Single bed. br br Bedroom 3: This room contains a Queen bed.br br Full Bathroom 2: Has a deep claw-foot tub, with shower.br br BASEMENT LEVELbr brLaundry: A washer and dryer are located in the basement level of the home.br brEXTERIORbr brThe private back yard has a grill, garden furniture and parking both at the top and bottom of the driveway.

Squam Light: Nestled in the heart of Annisquam

Gloucester, Massachusetts, United States

Bed

Bath

9

Sleeps

$390.11

Welcome to your private 2-bedroom guest suite in beautiful Gloucester, Massachusetts. This newly built and renovated 2025 downstairs suite was designed with a clean nautical beach vibe, giving guests a comfortable coastal stay close to downtown Gloucester, beaches, restaurants, shops, and local attractions.brbrThis is a great fit for couples, families, small groups, beach visitors, weekend travelers, and anyone looking for a clean, private, and convenient place to stay on the North Shore.brbrGuests have the private downstairs suite to themselves, including two bedrooms, a bathroom, living room, and private entrance. The upstairs living area is separately occupied and not part of the rental.brbrThe SpacebrbrThe first bedroom includes a queen-size bed and a wall-mounted flat-screen TV, perfect for relaxing after a day at the beach or exploring Gloucester.brbrThe second bedroom includes two bunk beds and its own wall-mounted flat-screen TV, making it a great setup for kids, family members, or extra guests.brbrThe living room is built for comfort and entertainment. It features a large 65-inch TV, video game console, sofa that converts into an additional sleeping space, and an electric fireplace table that adds a cozy touch to the room. Whether you’re watching a movie, playing games, or relaxing after a day out, the living room gives guests a comfortable space to unwind.brbrThe bathroom has modern upgrades, including heated floors, a wireless Bluetooth speaker fan, and blue LED lighting, giving it a clean and relaxing feel.brbrThe suite also includes a microwave, refrigerator, and coffee maker for drinks, snacks, coffee, leftovers, and light meals. Please note there is no full kitchen or stove.brbrLocationbrbrOne of the best parts of this property is the location. The house is close to downtown Gloucester and near many local restaurants, seafood spots, shops, and waterfront attractions.brbrGood Harbor Beach is about 7 minutes away, and Wingaersheek Beach is about 15 minutes away. Guests can enjoy the beach, fresh seafood, whale watching, harbor views, downtown Gloucester, and the classic New England coastal atmosphere without being far from the suite.brbrWhether you’re visiting for a beach trip, family getaway, weekend escape, sightseeing, or a relaxing stay near the water, this suite gives you a comfortable and convenient home base.brbrParking & AccessbrbrGuest parking is located at the back of the house. One parking space is provided, and up to two cars may fit if parked tandem-style and pulled forward enough. Additional street parking may be available nearby depending on the season, time of day, and local parking rules.brbrThe house is cream-colored with black shutters around the windows. Once you enter the driveway, drive toward the back of the house and turn right. The grey patio and private basement entrance will be right there.brbrGood to KnowbrbrThis is a private downstairs suite in a property with a separate occupied living space upstairs. The upstairs area is off limits and not included with the rental. The stairs leading to the second floor are locked, and the downstairs storage room is also locked and restricted.brbrExterior security cameras are located at the front and back of the house for safety and property security. There are no cameras inside the guest suite or in any private indoor areas.brbrWe respect guests’ privacy, but we are available by message if anything is needed during your stay.brbrGuests Will EnjoybrbrPrivate entrancebrNewly renovated 2025 suitebrNautical beach-style designbr2 bedroomsbrQueen bedbr2 bunk bedsbrTVs in both bedroomsbr65-inch living room TVbrVideo game consolebrSofa that converts into an additional sleeping spacebrElectric fireplace tablebrHeated bathroom floorsbrBluetooth bathroom speaker fanbrBlue LED bathroom lightingbrMicrowave, refrigerator, and coffee makerbrDedicated parkingbrClose to downtown Gloucester and restaurantsbrAbout 7 minutes to Good Harbor BeachbrAbout 15 minutes to Wingaersheek BeachbrbrThis private Gloucester suite is a clean, comfortable, and convenient place to relax, recharge, and enjoy everything the North Shore has to offer.

Private 2-Bedroom Gloucester Suite Near Beaches, Downtown & Restaurants

Gloucester, Massachusetts, United States