Vacation Home Rentals By Owner In Gloucester, MA

$1504.93

Timeless Seaside Estate: 4 Lodgings, Private Beach

Gloucester, Massachusetts, United States

9

Bed

5

Bath

14

Sleeps

$1021.12

/ Nightly

Private Vacation Home

Oceanside Estate: Main House & Apt w/beach access

Gloucester, Massachusetts, United States

Features:brbr☆ Waterfront home overlooking Ipswich Bay in Annisquambr☆ Expansive patio with breathtaking ocean viewsbr☆ On a 55 rolling acre estate of meadows, forest, marshgrass and rocky granite shorelinebr☆ The estate has walking paths that connect residents to various estate amenities, including two private beaches, a playground, and tennis court br☆ The estate home has 2 separate structures giving you plenty of space br☆ Board games and beach essentials included (towels, chairs, and an umbrella)br☆ Outdoor shower br☆ BBQ grill (gas and grill equipment included)br☆ Private workspacebr☆ Piano br☆ In-unit washer and dryer brbrLocation:br☆ 5-minute walk to a private white-sand crescent beach br☆ 5-minute walk to a private flat mica beachbr☆ 5-minute drive to The Cove Cafe br☆ 10-minute drive to Halibut Point State Park br☆ 15-minute drive to downtown Gloucester & Rockport (lots of restaurants, museums, galleries, and whale-watching!) brbrGuest Access br☆ The entire home and grounds are yours to explorebr☆ The beach and tennis courts are shared with other homes on the Bayview Estate - all related to one another. br☆ A lockbox with a key for you to use during your stay (instructions will be sent before check-in) br☆ You will receive a text with a link to Breezeway digital guidebook which contains helpful info for the home as well as food/local recommendations for Gloucester brbrParkingbr☆ Private driveway can comfortably fit multiple carsbrbrThe 2 separate structures are:brMain house - Center home with two floors brMonkey house - Apartment above garage with monkey decor, all one level brbrKitchen and Dining: brbrFirst Kitchen br☆ Fully stocked kitchen with cookware, dishes, toaster, microwave, drip coffee maker (with coffee and supplies), blender, stove kettle, and other essentialsbr☆ Dining room with long elegant table seating 10 people and ocean views brbrSecond Kitchen br☆ Fully stocked kitchen with cookware, dishes, toaster, microwave, drip coffee maker (with coffee and supplies), blender, stove kettle, and other essentialsbr☆ Small dining room seating 4 brbrLiving Room brbr☆ First Living Room br☆ Shared space with dining area br☆ Comfortable seating br☆ Small hidden TV with streaming br☆ Indoor Wood fireplace br☆ Ocean views br☆ Built in window nook br☆ BoardgamesbrbrSecond Living Roombr☆ TV with streaming br☆ Comfortable seating br☆ Splitter AC units br☆ Board games brbrBedrooms brbrBedroom 1 (Main house loft bedroom)br☆ (currently being renovated, photos coming soon) br☆ King bed br☆ Clothes storagebrbrBedroom 2 (Main house/ main level)br☆ King bed br☆ Beautiful ocean viewsbr☆ Work deskbr☆ Built in window nook br☆ Ceiling fanbr☆ Clothes storagebrbrBedroom 3 (Monkey house/ above garage) br☆ Queen bed br☆ Window AC unit br☆ Clothes storagebrbrBedroom 4 (Monkey house/ above garage) br☆ Two bunk beds (sleeps 4)br☆ Window AC unit br☆ Clothes storage brbrBathrooms br☆ Each house has a hairdryer br☆ Bathroom essentials included br☆ Main house bathroom on the main level has a step in shower and large vanity br☆ Main house half bath on main level br☆ Monkey house bathroom has a step in shower and separate bathtub brbrOutdoor Living br☆ Expansive brick patio with breathtaking ocean views, outdoor dining set, sun loungers and extra seating br☆ Walkable to 2 beaches, a playground, and tennis court (first come first serve basis) br☆ BBQ grill (gas and grill equipment included)br☆ Spacious yard around the house br☆ Outdoor games available brbrBaby & Family-Friendly Amenities br☆ Pack ’n play/Travel cribbr☆ High chair br☆ Baby bathbr☆ Kids games, books, and toys

Bed

Bath

Sleeps

$265.56

/ Nightly

Private Vacation Home

Large, open floor plan. Water views of Lanes Cove. Walk to Plum Cove beach.

Gloucester, Massachusetts, United States

This 950 square foot duplex one bedroom home is deceiving from the outside, once an old store in Lanesville Village now a village home overlooking the Cove. inside it is well appointed remodeled home featuring a large loft master bedroom upstairs and more sleeping and living on the ground floor. Air conditioning throughout~ though with the cove breezes it is unlikely you will need it. There is a large separate eat in kitchen with all the appliances, and almost everything else you may need downstairs.-BYOL (bring your own lobsters). Included are more conveniences, in the kitchen spices, and basic pantry items, in the bath- hair dryer,, towels and linens, a washer and dryer,. Our home features comfortable seating, games, books and more! Close to everything, yet a real vacation spot.br Walk a couple doors down to the package/general store for marinated meats and some wine, settle in on the deck to enjoy the famous sunset over Lanes Cove. Wake up and start at the Plum Cove cafe for coffee on your way to Plum Cove beach, never crowded! Great for families and sea glass hunting! Like a more rugged hike explore the wooded quarries of the Greenbelt - great on a hot day. Lots more a short drive away, like Rockport and Bearskin Neck, large beaches like Good Harbor, Wingarsheek, Cranes and more. Many people come to relax but if you want to visit Rockport, Salem or Boston they are easy to jump to- catch the train for a day jaunt to Salem or Boston a couple miles away (three stations to choose from), Rockport is just a mile up the road as you pass by Lobster Cove.We will consider your dog, but require a special dog security deposit. Dedicated parking for one car and street parking is always available. There is one granite step to enter, and stairs to the loft bedroom. Many guests enjoy the down couches and high Queen airbed downstairs for overflow

Bed

Bath

Sleeps

$977.38

/ Nightly

Private Vacation Home

The Aerie. 2 King beds, AC, outdoor shower. Walk to 2 local beaches

Gloucester, Massachusetts, United States

Welcome to Aerie! Enjoy this grand gathering house with great flow and enough rooms for all the beach lovers in your life. The home is situated between two of Cape Ann's most coveted beaches, Long Beach and Good Harbor Beach. As an added bonus the home is moments walk to an ice cream stand and pizza shop.brbrBeamed ceiling, paneled walls, and wood floors throughout provide period detail and create a traditional cottage vibe. The first floor includes an open concert kitchen and dinning area, a bath with stand up shower, a large living room with lots of seating, and a cozy den with fireplace. Laundry is also located on this level. There is also a finished, enclosed 1st level porch washed with natural light that opens onto a large exterior patio perfect for outdoor dinning and lounging. New for 2024 is an outdoor shower. brbrThe 2nd level has 8 bedrooms featuring two king bedrooms, and another full bath. Two of the front bedrooms room have distant ocean views. The four central bedrooms have central air. The rear two bedrooms and fronttwo bedrooms have portable air conditioners. In the winter the two front and rear rooms use electric heat. (Window units removed in early fall).brbrThe house can sleep 16 people in beds.brbrThe name Aerie means an elevated, secluded dwelling and this home is just that. This near 100 year old beach cottage is perched above Thatcher road making it a quick walk to local beaches. The large driveway, and an additional small lot across the street, allow guests to park up to ten cars.brbr*All bed Linens/bath towels are included. Beach towels are not provided. brbr———Extra Information————-br-Boomings last week of June-labor day require 7 nights stay Fri-fri. br-Guests are asked to maintain ability to communicate via VRBO app for notifications and updates. brbr-See our sister property listing on homeaway (#3641328). Sleeps 12 and is a quick walk to Goodharbor beach.brbr -We take our neighbors comfort and privacy very serious. If your group cannot handle being respectful of our neighbors and maintain quiet time after 10pm we ask you to please not book.

Bed

Bath

Sleeps

$1415.36

/ Nightly

Private Vacation Home

Stay at Good Harbor Beach

Gloucester, Massachusetts, United States

Summary:brbr4-Minute Walk to Good Harbor Beach!brbrbrbr✓ Prime Beach Road location just steps from iconic Good Harbor Beachbrbr✓ Brand new, top-to-bottom renovation with every detail thoughtfully reimaginedbrbr✓ Sleeps 18 across a spacious main house + private attached guest housebrbr✓ Designer-furnished throughout with all-new, high-end finishesbrbrbrbrThe main house features 4 bedrooms plus a bunk room, 3.5 bathrooms, and two laundry rooms. The attached guest house includes its own kitchen, bathrooms, and porch—ideal for added flexibility.brbrbrbrVisit @stay_collections on IG for a video property tour.brbrbrbrThe Space:brbrStep inside this fully renovated coastal retreat just a 4-minute walk to Good Harbor Beach. Thoughtfully redesigned from top to bottom, this home blends historic charm with elevated modern finishes, offering exceptional space, privacy, and comfort for large groups and multi-family stays.brbrbrbr☆☆☆ HIGHLIGHTS ☆☆☆brbrbrbr→ 4-minute walk to iconic Good Harbor Beachbrbr→ Sleeps up to 14 across a main house + private attached guest housebrbr→ Brand new renovation with all-new furnishings and finishesbrbr→ Private outdoor spaces + parking for 6 carsbrbrbrbr☆☆☆ MAIN HOUSE – LIVING SPACES ☆☆☆brbrbrbr→ Bright living room with exposed beams and refinished hardwood floorsbrbr→ Chef’s kitchen with induction range, wine fridge, and eat-in diningbrbr→ Front porch, back patio, private yard, and grillbrbr→ Designed for gathering and entertainingbrbrbrbr☆☆☆ MAIN HOUSE – SLEEPING ☆☆☆brbrbrbr→ Primary bedroom with king bed and en-suite bathroombrbr→ Two queen bedrooms + one twin bedroom (2 twins)brbr→ Bunk room with four twin beds and half bathbrbr→ 3.5 bathrooms totalbrbr→ Two laundry roomsbrbrbrbr☆☆☆ ATTACHED GUEST HOUSE ☆☆☆brbrbrbr→ Private entrance with enclosed porchbrbr→ Full kitchen with dishwasherbrbr→ King bedroom + 1.5 bathroomsbrbr→ Dedicated laundrybrbr→ Queen sleeper sofa (please inquire)brbrbrbrA rare opportunity to stay steps from the sand in one of Gloucester’s most desirable beach neighborhoods. Perfect for multi-family groups seeking space, style, and privacy — all moments from Good Harbor Beach.brbrbrbr Book today and experience Good Harbor Beach at its best.brbrbrbrGuest Access:brbrSmart lock door codes will be sent prior to arrival.brbrbrbrThe Neighborhood:brbrThis home is located in a quiet, residential coastal neighborhood just steps from some of Gloucester’s most iconic scenery. Directly across the street from Bass Rocks Golf Club, the area feels peaceful and established, while still offering quick access to everything Gloucester has to offer. Good Harbor Beach is a short walk away, the scenic Back Shore is just a 1-minute drive, and Downtown Gloucester is a lively 7-minute drive for dining, shops, and harbor views — the perfect balance of calm and convenience.brbrbrbrOther Things to Note:brbrThere are two queen pull out couches, please inquire. No pets, smoking, or events are permitted.brbrbrbrInteraction with Guests:brbrIf you need anything during or leading up to your stay, just shoot us a message and we are there to help!

Bed

Bath

Sleeps

$413.29

/ Nightly

Private Vacation Home

3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach

Gloucester, Massachusetts, United States

My husband and I want to assure you that we take your family's health and safety very seriously. Our house is professionally cleaned after each guest, to ensure your comfort. Our home offers self check in and keyless entry, and if you are more comfortable using your own linens and towels, please let us know and we will accommodate you. We want you to be able to relax and enjoy your vacation.brbrPlease enjoy our 3 Bedroom, two bath home, It sleeps 7 comfortably, with 2) queen size bedrooms, and one bedroom with bunk beds and a trundle. There is room for an extra person on our couch. Both full bathrooms have been remodeled, one features a walk in shower, and the other has a tub/shower combo. There is also an outdoor shower for your use after returning from the beach. brbrOur house does not have air conditioning. There are ceiling fans in the two master bedrooms, and tower and box fans for your use while you enjoy your stay. The open kitchen and living room floor plans have cross ventilation thru the front and back windowsbr brOur home features an open floor plan for the kitchen and living room, complete with skylights. Relax on the patio with your morning coffee or dinner and drinks. There is also a laundry room off of the kitchen with a washer and dryer for your convenience.br brAdditional amenities include two 55 smart TV's, one in the bedroom and one in the living area (use must use your Netflix account), an Xbox 1 (please bring your own games), WIFI, cable TV, an outdoor grill and patio furniture. All linens and towels are included.brbrIt is a short walk to Long Beach from our home (less that 5 minutes), and just a 10 minute walk to Good Harbor Beach if you are looking for a change of scenery.brThe house also offers plenty of parking space.brbrRockport's famous Bear Skin Neck, with all the art galleries, food and shopping you can enjoy is a bike ride or quick trip in the car downtown (less than 3 miles away).

Bed

Bath

Sleeps

$878.37

/ Nightly

Private Vacation Home

Waterfront Home! Stunning sunsets, swimming, paddling!

Gloucester, Massachusetts, United States

Located on the waterfront of Little River (offshoot of Annisquam) in Gloucester, Cape Ann, sweeping ocean river views, gorgeous sunsets, and a direct water access dock perfect for hanging out and watching the tide come and go. Swim to the raft, fish, kayak and paddle board (at high and medium high tide)! Kids love to look for crabs and snails at low tide. Watch the ospreys, egrets, herons and bald eagles fish. Nap, read or dine on the screened-in porch or in the patio/yard area overlooking the water. Close proximity to beaches - Stage Fort beach and park (5 min drive) and Good Harbor and Wingersheek beaches (12 min drive). Explore the many cafes, shops, bakeries, restaurants and nightlife in Gloucester center. Short drive to Halibat State park and Downtown Rockport. brbrLots of beds for your whole family! There are 3 bedrooms on the top floor and a fourth bedroom and bonus den/office on the bottom floor that can used for sleeping too. The three main bedrooms are on the top floor along with the kitchen, family room, full bath and porch. One bedroom overlooks the river with a king bed. A second bedroom has two twin beds side by side and a third twin bed, perfect for kids. The third has a full size bottom bunk and twin top bunk as well as a free standing twin bed. Below the main floor, in the walk-out basement overlooking the water, is a bonus den/office with a queen bed, couch area and desk as well as a bedroom with a queen bed and trundle twin beds. There is a rustic full bath with a standup shower, sink and toilet in the unfinished part of the basement near the bedroom, off the den. Washer and dryer are also on this floor. There is an outdoor shower to rinse off the salt water. brbrThere are two outdoor dining options - one on the patio by the walk-out den overlooking the river which seats 4-6 and the other is on the screened-in porch, off the living room, which seats 8 -10. Indoor dining seats 4. Renters can use paddle boards, dock and raft. Motor Boat, trampoline and fireplace not in use for guests. Please note the dock is removed seasonally.

Bed

Bath

Sleeps

$1173.48

/ Nightly

Private Vacation Home

Salt Marsh Cottage: Private Coffins Beach!

Gloucester, Massachusetts, United States

Salt Marsh is a large and comfortable vacation home with lush views that stretch across Farm Creek Marsh. This property also has rights to access private Coffin's Beach.brbrThe generous open-plan floor plan starts with the large eat-in kitchen and continues to the living room and library beyond. There is a pantry area off the kitchen that includes laundry and a half bathroom. Up a short flight of stairs is a newly-built game room with a daybed and trundle for extra sleeping space.brbrUpstairs, the Primary bedroom offers great views and a spacious full bath with soaking tub and separate shower, plus double sinks. Two additional bedrooms, one with twin beds and another with a Queen bed, and a full bath completes the second floor. The lower level has a large suite that sleeps four and includes a daybed and trundle, a Queen-sized Murphy bed, and a full bath with shower.brbrOutside, there are marsh and peek-a-boo ocean views from the lush backyard and from the oversized deck with a gas grill, dining set, and outdoor shower.

3

Bed

2

Bath

8

Sleeps

$377.32

/ Nightly

Private Vacation Home

Spy Glass - Views of Ipswich Bay

Gloucester, Massachusetts, United States

Perched on the third floor of a well-maintained building, this modern two-bedroom apartment offers comfort, convenience, and ocean views of Ipswich Bay.brbrInside, you'll find a thoughtfully updated space featuring a fully equipped kitchen with plenty of natural light. Whether you're relaxing with a book or preparing a home-cooked meal, this home is designed with ease and enjoyment in mind.brbrStep outside and explore all that Lanesville has to offer—scenic Lanes Cove and Harvey Reservation, coffee shops, and scenic walking trails. Best of all, you'll be just a few hundred yards from Plum Cove Beach, a quiet, family-friendly beach.brbrWith one off-street parking space and a peaceful coastal setting, this apartment is ideal for couples or small families looking to unwind by the sea.brbrNo Pets. No smoking. No events or parties.

Bed

Bath

Sleeps

$722.58

/ Nightly

Private Vacation Home

All-Season Beach Haven - walk to two beaches!

Gloucester, Massachusetts, United States

If you don't know Gloucester, a stay at our Beach Haven is the best way to experience it - and if you do know it, you'll appreciate the access to great views, perfect light, and a wonderful little town. Read on...brbrThe house: A very short walk to Gloucester's two best beaches, Good Harbor & Long Beach, our Beach Haven has breathtaking views from the living room and spectacular roof deck. (No busy roads to cross to get to the beach.) From the deck, you can enjoy your morning coffee or dinner & cocktails while breathing the sea air and watching the waves over Salt Island. The roof-top shower lets you gaze at the clouds and feel the ocean breeze while washing off the sand after a long day at the beach. A perfect respite from your busy days.brbrThe town: We also highly recommend a trip or two to the wonderful harbor/fishing town (10 min drive) for super fun and eclectic shopping, more than a few casual or elegant restaurants and cafes, museums, whale watching excursions and more. This 400 year old port has a deep, proud history - never a dull moment. We absolutely love it here and so will you. Come visit!

Bed

Bath

Sleeps

$659.4

/ Nightly

Private Vacation Home

Waterfront Home with Spectacular Viewsof the Annisquam River

Gloucester, Massachusetts, United States

Watch the beautiful sunsets over the Annisquam River from the deck or just enjoy the scenic views all day long of Merchants Island, Jones Creek and Wingaersheek beach at a distance. Simply spectacular. brbrThis vintage home built by a boat captin in the 1890’s has six bedrooms on the second floor and sleeps up to 10people. Large eat in kitchen with two seating areas. There is a half bath off the kitchen, and a bathroom with a tub on the second floor. The walk out lower level has a newer bath with shower and laundry. You may swim from the property or boat from the shore or dock with a canoe, kayak, flippers, mask and snorkel and get ready for a fabulous vacation. (We do not supply any of thesebrItems). brKeywords: Single Family

Bed

Bath

Sleeps

$739.86

/ Nightly

Private Vacation Home

Two Beaches: Long Beach & Good Harbor

Gloucester, Massachusetts, United States

Ideally situated between two of Cape Ann's most beautiful beaches, this ideal vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to Good Harbor Beach. The home has a single level and an open floor plan that offers convenience and practicality.brbrThe location for this beach house is especially convenient to many local amenities. In addition to the beaches, in one direction there are super markets, coffee shops, family restaurants and the rest of Gloucester beyond. In the other direction is Rockport, with it famous village center of shops, eateries, art galleries, and the Shalin Liu performance center.brbr1,402 Sq. Ft. No pets. No smoking.brbrLiving Room: A sunny room with large windows, this room contains a 55” flat screen TV, a decorative fireplace, a large sofa, and a rocking chair.brbrKitchen: The kitchen contains granite counter tops, recently updated stainless appliances, and a gas range. The kitchen opens on to the adjacent dining room.brbrDining Room: Dining area seats 6 and is between the kitchen and living room.brbrSun Room: This bonus room is filled with light with a pull-out sofa for additional sleeping space. There is also a card table and a sliding door to the back yard and deck.brbrFull Bathroom: Contains both tub and shower.brbrHalf Bathroom: Doubles as the laundry room, with the washer and dryer.brbrBedroom 1: Master bedroom with King bed and a sliding door to the deck.brbrBedroom 2: Queen bedroom.brbrBedroom 3: Queen bedroom.brbrEXTERIORbrbrThe deck overlooks the spacious yard and features a patio dining set with an umbrella for shade. There is also a gas grill, additional outdoor seating, and a cold-water outdoor shower to rinse off the sand after the beach.brbrPARKINGbrbrThere is a circular drive that can accommodate 4 cars.

Bed

Bath

Sleeps

$1025.21

/ Nightly

Private Vacation Home

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

Gloucester, Massachusetts, United States

This is the vacation house you have been looking for! It’s perfectly located only a few steps from the private & secluded section of Coffins Beach. As well as a short walk to the world famous Wingearsheek 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 2-3 min minutes walk, less than 2/10th of a mile to the private neighborhood section of the beach called Coffins beach. Or 1/2 of a mile to the white sands of the public side of Wingaersheek Beach. This immaculate and graciously appointed home is the perfect destination for discerning beach lovers who want only the best in accommodation, sea & surf, at the same time having the secluded privacy you have been dreaming of.brbrHousing accommodations are a perfect set-up for the extended family or share with the best friends. This location contains 3000 sq/ft. of housing for your enjoyment. This is one of the most private and secluded houses available in the area, as you will be quietly resting on 1.38 acres. Once you enter the private community by way of the guarded gate house and continue until Sleepy Hollow Pond you will turn on to your own private way and head up the driveway to the house, and you will immediately feel like you are on vacation and ready to enjoy your stay. All the while as it seems you are the only one around. You will be residing on your own 1.38 acres of private land. There are numerous outdoor custom built landscapes and a front patio to enjoy the beautiful weather and enjoy the wonderful privacy. As you walk-in the first floor entrance into the spacious custom tiled foyer/entrance, you will immediately feel the beach house charm! The first floor also contains an expansive open concept fully appointed eat-in gourmet kitchen featuring double built-in Jenn-Air ovens. The granite counters, custom cabinets, complete with Built-in counter blenders, and coffee grinder, 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 open concept, eat in kitchen, you can relax as you proceed thru to the spacious living room which contains the center-piece of the room, a beautiful custom stone built fireplace. Enjoy watching the 55” HDTV with the full surround system and music surround system (iPod friendly), or choose to relax in quietness, as the choice is yours. To your right you have two oversized custom French doors to the enormous and fully screened-in rear deck which has some spectacular water views over looking Sleepy Hollow Pond, which is a brackish pond teaming wide life. This is the prefect spot where you can relax on the outside deck furniture and sunbath privately instead of the beach if you prefer. As you continue around the first floor, there is the first of the three very nice bathrooms. For the more formal dining experience, you can always entertain in the Formal Dining room, if you prefer. You will also find the separate laundry area off the kitchen entrance/foyer. As you climb the stairs to the Lower Level. You will enter into the entertainment area which contains a large TV, and a spacious and comfy living room sets, and don’t forget you can always challenged each other at the 3-in-1 game table, with your choice of pool, ping pong and air hockey. Perhaps you prefer to play Xbox with your friends and family, and of course bring some family favorites, or sit at the beautiful Oak table and play table games or have a card tournament. It’s a great space while you’re not enjoying the beach. Additionally the sectionals do contain sleeping arrangements which can be used once the fun has ended! Once you are back on the main level and you climb the stairs to the second floor you will find the king sized master bedroom with cathedral ceilings It contains your own custom full-sized bathroom and another queen-size sofa set, and a large TV. The King size bed actually looks small in this space! There also is a huge second king size bed room, and an additional bedroom with Two Bunk beds set ups, one with pull-out trundle to round out the sleeping arrangements. The third full size custom bathroom is also located between the two bedrooms. In addition to the three bedrooms on the second floor, we also have a very large beautiful bedroom with a queen size bed in the loft over the garage, which gives you the added ability to have an another extra bedroom to fully round out this wonderful location. The house is air conditioned, if you prefer, or you can enjoy the sea-breeze air and open the numerous oversized Anderson windows. For those of you who need to always be connected, the house has WiFi, of course, but brings your cell phone as there is no landline at the house. Plenty of parking in the U- shaped driveway and lovely landscaping outside! Additionally, Gloucester is quickly becoming artwork-culturally friendly area. Take a ride to the local artwork shops found around Rocky Neck. Find a new treasure for your home to remember your trip or come every year if you prefer.brMore pictures and information available. Please make a request or make a suggestion. There is everything you would expect for a great ocean beach stay, located only 10-15 minutes drive to Gloucester harbor. Electric Beach/Golf cart provided with house. 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!brbrNew in 2013.. Exciting news, we are adding a Classic restored 1965 Pontiac GTO or a 1986 Tran Am WS-6 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.brNOTE: If you are looking for an additional house/property, Please view our beautiful sister-house (Homeaway Listing number: 951090 or VRBO Listing number: 391707 ) Located only 1/3' of a mile away, and located in the private section of the beach as well.brbrAbsolutely NO smoking or Pets allowed. For the safety and comfort of all current and future guests.brPlease 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.

Bed

Bath

Sleeps

$3718.4

/ Nightly

Private Vacation Home

Edgemoor Estate - 11 Bed/6.5 Bath (Sleeps 28) - Heated Pool Jacuzzi Beach

Gloucester, Massachusetts, United States

Welcome to your ultimate coastal escape at this magnificent, fully-renovated brick mansion on Eastern Point in Gloucester, MA. Perfectly set up to host groups of up to 28 guests across 11 luxurious bedrooms and 6.5 baths, this estate is a rare and coveted find for gatherings or high-end retreats. Perched atop a lush 1.6-acre hilltop and just 100 yards from the beach, the property combines breathtaking ocean views with a serene, private setting surrounded by historic stone walls and dramatic granite outcroppings.brbrPart of the ZenDen Escapes Luxury Collective on IG @zendenescapes.brbrInside, you’ll find timeless elegance with soaring ceilings, grand windows flooding each room with natural light, and ample space for dining, entertaining, and relaxation. Recent renovations bring modern comfort, from a new heating system to an EV charger, 50+ new windows, and a whole-home generator, ensuring a flawless stay. The gourmet kitchen and updated bathrooms boast tasteful finishes that complement the mansion’s refined character, making every moment of your stay feel elevated.brbrOutside, the property shines with its manicured grounds, heated saltwater pool, and spa, providing a luxurious oasis perfect for lounging and unwinding on sunny days. A separate guest house (which can be booked separately) offers additional privacy and convenience, while the pool area invites you to soak up the sun or take a refreshing swim, surrounded by landscaped gardens that add a touch of peace and privacy.brbrWhether you’re gathering in the spacious living areas, savoring gourmet meals in the elegant dining room, or stepping out to explore the stunning beaches just steps away, this property offers an extraordinary setting for an unforgettable coastal retreat. Indulge in the timeless charm and ultimate luxury of Gloucester’s finest short-term rental—your private paradise awaits. zen den escapes d o t com

Bed

Bath

Sleeps

$789.45

/ Nightly

Private Vacation Home

Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit

Gloucester, Massachusetts, United States

brWelcome to your very own summer beach home! Located a short 3 minute walk from good harbor beach, this two level single family home offers five bedrooms, two bathrooms and an open concept kitchen, living room and dinning room with an additional living space on the lower level perfect for the kids. The grounds include parking for up to six cars, an outdoor entertaining/dinning area, and spacious fenced in yard for the kids to run around in. It's the perfect home for a large group or family traveling together.brbrInside you will find comfortable furnishings and all the necessary items to make your stay enjoyable. Onsite amenities include but are not limited to: Wi-Fi, Washer and dryer, fully stocked kitchen with dishes and cookware, two televisions with app/ streaming services and a bunk bed set up for those traveling with kids. Don't forget the outside shower to get all that sand off after a day on the beach.brbrThe top floor features an open concept living room, dinning room and kitchen as well as two bedrooms and a bathroom. The master located on this floor has a king bed and small balcony overlooking the marsh. Another smaller bed off the kitchen has a twin over full bunk bed. A large deck off the living room overlooks the fenced in yard with fire pit. All rooms on this level have ductless AC. brbrDownstairs you'll find 3 bedrooms, a small tv area and another full bathroom. The bedrooms on this level consist of 2 queen beds and 2 twin beds. All of the bedrooms have window air conditioners (window units are in place Memorial Day-labor day) . The living room has a ductless wall unit. The laundry room is also located on this level.brbrAside from the accommodations, what will keep you coming back year after year is the unbelievably short walk to Good Harbor beach. You can be on the beach in minutes, and you'll welcome the short walk back after a relaxing day. brbr**Linens/towels are NOT provided (we do supply pillows, blankets and mattress covers). Please see the house manual/welcome email for needed items. brbr*Pets are not permitted at the property. brbr*From June 24-August Check in day will be FRIDAY**brbrPlease about our sister property which can accommodate 16!br

Bed

Bath

Sleeps

$684.56

/ Nightly

Private Vacation Home

Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access

Gloucester, Massachusetts, United States

This finely maintained summer cottage built in the 1820s overlooks Hodgkins Cove in Gloucester Massachusetts.brbrUnique and special amenities include 2 private beach accesses, consistently spectacular sunset views over Hodgkins Cove and Ipswich Bay, and hiking/walking paths on a 55 acre private estate (yes really!).brbrIt comfortably sleeps 11, has 5 bedrooms, 2 and a half bathrooms, a downstairs porch, and and upstairs nightclub (which is a covered screened in outdoor lounge area great for evening cocktails to watch the sunsets).brbrIt's located 5 miles from Bearskin Neck in downtown Rockport and 5 miles from downtown Gloucester. Both downtowns are filled with very nice, family restaurants, fun boutiques, and art galleries. brbrEnjoy water views from most rooms in the house. Dogs allowed, smoking not allowed.brbrFIRST FLOOR:brbrKitchen: Everything you need in a kitchen: range, sink, dishwasher, silverware and plates and pans, and of course ocean views.brbrBathroom 1: sink, toilet, shower/bath.brbrBedroom 1: King bed, closet, ocean views.brbrDining Room: Dinner table that seats 10 comfortable.brbrLiving Room: Television, 2 couches, antique day bed, fireplace, and an ocean view.brbrUtility Porch: Washer/DryerbrbrBay View Downstairs Porch: Overlooks Hodgkins cove. Beautiful views. Perfect for enjoying a nice day.brbrbr2ND FLOORbrbrBedroom 2 (the door room): 3 twin beds, 1 closet, 2 dressers. Great for kids.brbrBathroom 2: sink, toilet, bathtub.brbrBedroom 3: full bed, closet, ocean view.brbrBedroom 4 (the pillow): a smaller, cozy room with a full bed. Ocean view. brbrBedroom 5 (the master): king size bed, closet, half bathroom, sitting area, and of course ocean views.brbrBathroom 2.5: sink and toilet in the master bathroom.brbrUpstairs Porch (the nightclub): screened in, couches, and a swinging Gloucester hammock. Great for cocktails in the evening and for a fantastic sunset.

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$526.45

/ Nightly

Private Vacation Home

2BR/2BA Harborside Home · Fenced Backyard · Ocean View ·Walk to Rocky Neck+Beach

Gloucester, Massachusetts, United States

. - Sunny and cheerful home with direct views of harbor, boating activity & glorious sunsets from your private deck & living spacebr- 1 mile to all the attractions of Downtown Gloucesterbr- Located in the quaint East Gloucester neighborhood walking distance to Rocky Neck art galleries and restaurantsbr- 1 mile to either Good Harbor Beach OR Niles Beachbr- Hi-speed WiFibr- Fully fenced in backyardbr- Free washer/dryerbr- Fully equipped + stocked kitchen brbrRare opportunity to experience an authentic Gloucester vacation right on the harbor! Conveniently pull into the street parking spots and step up to your front deck overlooking the specular harborside. Upon entering the recently updated duplex you'll immediately be greeted by all the light and bright coastal colors and details. brbrOn the first floor you'll find a newly renovated and fully equipped kitchen complete with stainless appliances and complementary coffee and tea. Head into a comfortable living room with smart TV to stream your favorites. Curl up on the spacious bay window seating with plenty of books to explore and enjoy harbor views. The first floor also has a full bathroom and a washer and dryer.brbrHead up the stairs and you'll find 2 coastal style bedrooms with queen beds and a full bathroom. In the largest bedroom you'll wake up to unobstructed views of the harbor! In the backyard you'll find a lovingly cared for lawn with gardens and private deck for al fresco dining & summer grilling. The yard is fully fenced in making it perfect for letting little ones run around!

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$1119.89

/ Nightly

Private Vacation Home

Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil

Gloucester, Massachusetts, United States

This is the Vacation Beach House you have been searching for. Perfectly located only steps to Long Beach Gloucester, this immaculate and graciously appointed home is the perfect destination for discerning beach lovers who want only the best in accommodation, sea & surf! The house has direct waterfront views of the private section of Gloucester’s side of Long beach as well as direct views of the Twin Lighthouses of Thatcher’s island, which is a well known spectacular tourist view. Enjoy your favorite part of the day gazing out at the beautiful scenery. All this while less than a 2 minute drive (8-10 minute walk) to the World Famous Good Harbor Beach. You can enjoy both beaches during your stay. Why would you settle for one beach when you can enjoy two This beautiful home boasts 5+ lovely bedrooms and 3 sparkling custom tiled full baths as well as fabulous extras like a family room with a big screen TV and 3 in 1 gaming table, formal living room, Fully open concept first floor formal dining room, and gourmet kitchen, with ocean views from many parts of the house. The outdoor space of this house is just as amazing with large outdoor decks and two fully expanding canopies which only add to the space and charm of this location. Relax on the patio, or recharge for a bit on the outdoor hammock. All within 50 yards to the white sands of Gloucester’s side of Long beach. You won’t want to leave!brHousing accommodations are a perfect set-up for the extended family or share with the best of friends. This location contains 3500+ sq/ft. of housing for your enjoyment. This is one of the largest houses available in the area. On your drive to the house you will pass by Good Harbor Beach and there is no question that you are at the ocean as the breeze and surroundings are undeniable. As you continue only a short distance you will turn into the private area of Gloucester’s section of Long Beach. After a few short turns you will arrive to the house, and you will immediately feel like you are on vacation and ready to enjoy your stay. Outdoors you will notice the numerous outdoor custom built landscapes and a large rear yard with patio to enjoy the beautiful weather and enjoy the wonderful privacy. As you enter the house at the first floor into custom tiled entry you will immediately feel the beach house charm! Prepare to be amazed at the open concept Kitchen, Living room and Dining area which are perfect for the family gatherings and the memory making event you are visiting for. The custom hardwood stairwell is impressive and the detail is outstanding, as it blends into the hardwood flooring on the entire first and second floor. The Kitchen, while fully appointed, has a full granite surround with a bar level set-up for sitting down for a nice quick meal while the dining area is perfect for the larger sit down style dinners. The expansive custom built-ins and full appliances complete 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, it’s all up to you. The living room is just amazing for relaxing and watching the ocean, or watching TV if you prefer. Additionally on the first floor we have a full bathroom and a spacious bedroom containing a Queen-size bed with a pull-out trundle. As you ascend to the top of the beautiful custom staircase to the second floor the view of Long beach with the Twin light houses of Thatcher’s Island in the background will astound you. The top of the stairs lead to another living room a huge custom designed sectional with the breath-taking ocean views, as well as a 55” HDTV and gas fireplace. The sectional includes a pull out twin size bed. It really is an amazing space to just relax and enjoy your time. Just off this living room is the master bedroom which contains a majestic King Size bed, a 55” HDTV and your own private deck with outdoor furniture and fully automatic expanding awning. Have your morning coffee on the deck overlooking the picture perfect private back yard. As you exit the master bedroom thru the oversized French doors onto the deck you will notice a hand painted seascape mural by one of the very famous local artists. It’s a great touch and just adds so much charm! We also have an additional bedroom/nursery off the master for those who want to have the kids close by. This bedroom/nursery contains a twin bunk bed with a trundle. Also on the second floor is the master bathroom with many custom features including a Jacuzzi tub and separate stand up shower. If you ever do decide to leave this upstairs retreat, and head back down the stairs to the main level you can still proceed to the lower level for even more entertainment. The lower level contains the washer/dryer and laundry area, as well as two more bedrooms and an additional Living room with a kitchen/kitchenette and another full bathroom. The bedrooms are spacious and well appointed, one bedroom contains a Queen bed with an additional twin bed with trundle and the other bedroom contains a twin bed with trundle and a second twin bed. The Living room has a large Queen-size pull-out sofa coach. Don’t forget you can always challenged each other at the 3-in-1 game table, with your choice of pool, ping pong and air hockey. Perhaps you prefer to play Wii with your friends and family, and of course bring some family favorites, or sit at the beautiful Oak table and play table games or have a card tournament. It’s a great space while you’re not enjoying the beach. There is also a walk-out slider to the beautiful yard as well with easy parking and access if required. You can have plenty of room with friends and family but never feel like you are crowded. This also makes an excellent area for in-laws, an au pair, or a family with small children that need a bit more privacy. For those of you who need to always be connected, the house has WiFi, of course, but brings your cell phone as there is no landline at the house. If the house is not big enough already and you need more space, then the outdoor area is the place for you! This is the perfect spot where you can relax on the outside deck furniture and sunbath privately instead of the beach if you prefer. We have a full patio arrangement for you with a fully expanding automatic awning as well as a relaxing hammock, which seems to draw you to some downtime! There is an outdoor shower with hot and cold water to rinse everything off and we do have an outdoor grill of course! The large driveway is spacious enough for 5 or 6 vehicles. with plenty of parking. Additionally, Gloucester is quickly becoming artwork-culturally friendly area. Take a ride to the local artwork shops found around Rocky Neck. Find a new treasure for your home to remember your trip or come every year if you prefer. We would love to have you visit our home!brMore pictures and information are available. Please make a request or make a suggestion. There is everything you would expect for a great ocean beach stay, located only a 5-10 minute 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

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$595.73

/ Nightly

Private Vacation Home

First Period Colonial Lodging in Gloucester MA

Gloucester, Massachusetts, United States

As you step through the threshold of this sensitively restored 1680 residence, you are transported to an earlier time—immersed in the history of the home and the area. One of the oldest homes in the Essex corridor, the interior of the William Haskell House has remained virtually untouched since it was built and is documented as one of the finest examples of a First Period Colonial house that exists today.brbrIf you are a lover of period antiques, historic old homes, American history, and seek a truly unique experience—then a stay at the William Haskell House is for you! You will sojourn amid historically significant antiques, in a home that has been meticulously conserved to reflect the aura of the original 17th century structure.

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$665.76

/ Nightly

Private Vacation Home

Stay at Niles Beach

Gloucester, Massachusetts, United States

Summary:brbr✔ Great location: 3 min walk to Niles Beachbrbr✔ 5 beds: king, queen, 3 twins (2 baths)brbr✔ Fully equipped kitchen and diningbrbr✔ 3-car parking, EV charger*brbr✔ Hassle-free check-out, leave the chores to usbrbrbrbrSituated between Rocky Neck and Eastern Point, explore Gloucester and Greater Cape Ann easily.brbrbrbrNewly renovated, designed for comfort. Enjoy hotel-like amenities with the convenience and togetherness of a home! Visit @stay_collections on IG to explore our property gallery and local recommendations!brbrbrbrThe Space:brbr☆☆☆ 1ST FLOOR ☆☆☆brbrbrbr→ Kitchen: Fully-stocked with essentialsbrbr→ Dining: Kitchen bar and dining tablebrbr→ Living room: Smart TV equipped with Netflix subscriptionbrbr→ Sun room: Sofa, coffee table and reading chairbrbr→ Bathroom: Full bathroom with bath tub and stand-up showerbrbr→ Note: Fireplace not in usebrbrbrbr☆☆☆ 2ND & 3RD FLOORS ☆☆☆ brbrbrbr→ Primary suite: King bed with ocean views, balcony, en-suite full bathbrbr→ Secondary bedroom: Queen bed, private deck, personal workspacebrbr→ Laundry: Convenient access to washing machine and dryerbrbr→ 3rd floor: Bunk room with 3 twin beds and ocean viewsbrbr→ Note: all bedrooms have window blinds and air-conditioning units (seasonally)brbrbrbr☆☆☆ OUTDOORS & PARKING ☆☆☆brbrbrbr→ Patio: Dining table with seating for 6brbr→ Grill: Fully equipped propane grillbrbr→ Garden: Flower beds with bench seatingbrbr→ Parking: Up to 3 vehicles (2 in driveway, 1 along the side) with a Level 2 EV charger (Tesla & non-Tesla compatible). Please note: the street and driveway are narrow, so larger SUVs may find maneuvering challenging.brbrbrbrAccessibility brbrThere are steps throughout the property as well as a tight staircase to the second floor that may make it more difficult for people with mobility issues to navigate throughout the house.brbrbrbrGuest Access:brbrGuests have access to the entire house with the exception of three closets that contain supplies and mechanical equipment for the property.brbrbrbrThe Neighborhood:brbrJust a three-minute stroll from the residence, Niles Beach offers a serene, family-friendly shoreline—an ideal escape from the typical tourist crowds. Nearby, Eastern Point Lighthouse and Good Harbor Beach are just minutes away, whether you’re in the mood for a scenic walk or a short drive along the coast.brbrbrbrLess than a mile away, the Rocky Neck Art Colony invites you to explore its vibrant mix of galleries, working artists, and charming waterfront cafés. For outdoor enthusiasts, Ravenswood Park features tranquil hiking trails that wind through quiet woodlands and salt marshes—perfect for a peaceful nature retreat.brbrbrbrWhen it comes to dining, enjoy local flavor at The Causeway, a laid-back favorite for generous seafood plates, or elevate your evening with authentic Italian fare at Tonno, located in the heart of Downtown Gloucester.brbrbrbrOther Things to Note:brbrOur home includes a narrow staircase—consider this if mobility is a concern for a comfortable stay.brbrbrbr*Please give us a heads up if you would like to utilize the EV charger. Usage rates will vary based on the length of stay.brbrbrbrOnce a booking is confirmed, the following cancellation policy is immediately 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.

3

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2

Bath

7

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