House vacation rentals in Gloucester

4.99 out of 5 average rating, 174 reviews

A modern living area features vaulted ceilings and wooden accents, creating an open atmosphere. A large flat-screen television is mounted on a white media console. Comfortable seating is provided on a dark sectional sofa, complemented by natural light from skylights and windows.

Home in Plum Island

“Salty Girl” Plum Island, MA

We Love our little “Salty Girl!”. She is a 2 bedrooms 1 bath family friendly open concept single family home with parking for 2 cars. The spacious deck off the back of the house has a table and a sectional outdoor sofa for enjoying the breeze and the sun! 3-5 minute walk to the beach or a 1 minute walk over the The Basin for the most unbelievable sunsets. Downtown Newburyport is a 10 minute drive or a 20 minute bike ride. We are licensed and inspected by the city of Newburyport as a legal STR.

4.91 out of 5 average rating, 141 reviews

A spacious outdoor deck features a white railing, providing a clear view of the expansive marsh and river landscape. The sky is bright and blue, enhancing the natural beauty of the surrounding greenery and water.

Home in Salisbury

NEW 3BR home, incredible views - Beach across St

Enjoy sunrises and sunsets with an expanse of windows that offer breathtaking views of the river and marsh in a new construction, BEAUTIFUL, single family home. Over 2000 Sq Ft wTile & hardwood floors. 1st level has Open living room/kitchen, half bath & 1 bedroom. 2nd Floor has 2 bedrooms, bath, laundry & Large outdoor deck. Beach is a 2 minute walk across the street. 10 minutes to Browns Seafood restaurant, Ice Cream, Groceries & more. 2+ Parking spots. We follow the Advanced Clean Protocol.

A welcoming living area features a comfortable gray sofa paired with a vibrant blue armchair. Natural light fills the space through multiple windows, highlighting the wooden ceiling beams. A dining table with two chairs sits nearby, complemented by decorative art and an accent rug.

4.98 out of 5 average rating, 108 reviews

Historic Luxury Renovation Walk to Town!

Come visit a very special home this winter! Stay at the 1767 Tuck House, where historic charm meets quintessential New England luxury! This is the perfect home for groups. Steps to the beach, shops, restaurants and arts. Home offers the privacy of boutique hotel with modern comforts: plush Casper mattresses, AC, 4K TV, laundry, heated floors, quartz counters, new appliances, 3BR, 3 Full Baths, 2 Kitchens, 2 Decks, Private Entries. A true Rockport gem, we promise a special stay.

4.83 out of 5 average rating, 213 reviews

The exterior of a two-story home is shown, featuring beige siding and multi-pane windows. A well-maintained front yard includes patches of grass and decorative bushes. A staircase leads to the front porch, with a fenced yard visible in the background, surrounded by trees for added privacy.

Home in Georgetown

Nothing Fancy Older Pet Friendly Home – near I-95

Enjoy your very own country living retreat! Our pet friendly home sleeps 8 with a large fenced in yard, so bring the kids & furry friends. There is a big backyard and lots of trees providing privacy. The fence is older but secure enough for your pets. Guests please know this is an older house inside. The finishes are older and cheaper. We are 1 min from I-95 & within 15 minutes of restaurants, golf course, & wedding venues. Guests that are very sensitive to smell should not book this place

A charming white house is positioned along a rocky shore, showcasing a four-season porch with large windows that provide views of the harbor. Lush greenery surrounds the property, complementing the tranquil water scene with boats in the distance.

4.93 out of 5 average rating, 174 reviews

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

4.93 out of 5 average rating, 308 reviews

A cozy living area is presented, featuring a modern black sofa and two soft pink ottomans. Natural light streams in through the window, illuminating the space. Decorative shelves with plants and artwork add a touch of greenery and charm to the room.

Home in Stoneham

Entire Apartment in Stoneham

Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

The exterior view of the home reveals a modern wooden structure surrounded by lush greenery. A spacious deck extends from one side, while stone pathways weave through well-maintained gardens. Soft blue skies and gentle clouds create a serene atmosphere.

4.97 out of 5 average rating, 145 reviews

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

4.98 out of 5 average rating, 344 reviews

A cozy living room features a white-brick fireplace, with a functional gas flame. Stylish furniture includes a patterned armchair and a soft couch, complemented by a light-colored striped wooden floor. Large windows allow natural light and offer views of the surrounding area.

Home in Rye

*Beachfront* Vintage Coastal Cottage - Relaxation

It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here: https://bit.ly/3vK5F0G We've outfitted it with an extra screen and a setup to get you up and running. Google home and Sonos systems bring this 100 year old beauty into this century.

A charming cape house is viewed from the street, featuring a covered porch with white railings. Large windows allow natural light to fill the interior. The surrounding yard is flat and grassy, bordered by trees that provide shade in a peaceful neighborhood.

4.91 out of 5 average rating, 135 reviews

Gloucester Beach House, near Good Harbor Beach!

Escape to this inviting, and pup friendly 4-bedroom Gloucester home, just a short walk to Good Harbor Beach! This classic coastal home blends comfort & convenience. All 4 bedrooms are air-conditioned, featuring a large eat-in kitchen, covered front porch perfect for relaxing or grilling, full bathroom plus refreshing outdoor shower. Stay connected with high-speed Wi-Fi, & enjoy the ease of on-site laundry. Openings for September and October. Ideal for weekend get aways!

4.93 out of 5 average rating, 176 reviews

The kitchen features navy blue cabinetry and modern stainless steel appliances, including a microwave and oven. A white countertop contrasts with the dark cabinets, enhancing the space's elegance. Natural light flows in through the windows, creating a bright atmosphere, while a small rug adds a decorative touch.

Home in Malden

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free

Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dinning and Large Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Laundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

A bright living area features large windows with views of a garden and ample natural light. A comfortable dark sofa and a plush chair are arranged around a glass coffee table on a colorful area rug. A wooden dresser and a small dining table add warmth to the space.

4.97 out of 5 average rating, 351 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.

4.98 out of 5 average rating, 105 reviews

A large tree with a broad canopy dominates the lush backyard, surrounded by greenery. The area features a stone border outlining a patch of grass, with glimpses of the landscape beyond, including wooded areas and a play structure in the distance.

Home in Danvers

Large, Comfortable & Conveniently located Home

You will be close to everything when you stay at this centrally-located private, updated historical home. 4 bedrooms & 2 baths w/plenty of extra space for large families or groups. Fenced-in spacious patio with huge backyard. Sizable, private parking area. Near Routes 95 & 128. Only 25 mins to Boston. Perfect for trips to picturesque points, including Boston, Gloucester, Newburyport, Rockport, Cape Ann, historic Salem & Maine coastal towns and cities. Dog friendly.

Popular amenities for Gloucester house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 23 reviews

A welcoming living area features a large yellow sectional sofa, paired with woven chairs. A colorful area rug anchors the space, complemented by a light wood floor. The walls are adorned with a tropical mural, and a kitchen area is visible in the background.

Home in Hull

NEW! Walk To Beach! Sunshine House

4.94 out of 5 average rating, 174 reviews

A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.

Home in North Andover

Nana-tucket Inn

4.98 out of 5 average rating, 63 reviews

An indoor pool is surrounded by light blue walls and gray tile accents. Natural light filters in through large windows, illuminating the water's surface. Steps lead from the pool to a door that opens to the outside area.

Home in Hampton

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

5 out of 5 average rating, 32 reviews

Home in Newton

Elegant & Spacious~Easy Boston Access! STR-25-22

A well-maintained backyard features a spacious pool surrounded by a green lawn and landscaping. The red house extends with multiple levels, showcasing a deck and seating area. Additional structures are visible, set against a bright sky, creating a serene outdoor environment.

4.89 out of 5 average rating, 27 reviews

Rockport Pool House|4BR/3BA Walk to Bearskin Neck

4.95 out of 5 average rating, 21 reviews

A light-filled living room features a soft white couch adorned with blue and aqua cushions. A cozy navy chair complements a glass-top coffee table, which is surrounded by patterned poufs. An air conditioning unit and a television are positioned for convenience, enhancing the inviting space.

Home in Hampton

Sleeps 10-4/2 Cozy Beach Cottage, Pool, Porch, BBQ

4.96 out of 5 average rating, 46 reviews

A well-maintained swimming pool is featured in the backyard, surrounded by a patio. Lush greenery and mature trees offer privacy. The two-story house is visible in the background, with large windows allowing light to enter. A basketball hoop is positioned adjacent to the pool area.

Home in Arlington

Beautiful Spacious 4BRM House!

4.97 out of 5 average rating, 107 reviews

Home in Weston

Spacious vacation unit in premium suburban town

Weekly house rentals

4.93 out of 5 average rating, 57 reviews

A bright and airy living area features large glass doors offering panoramic views of the water. Comfortable seating is positioned to take advantage of the scenic landscape, while light-colored walls enhance the spacious atmosphere. A ceiling beam adds architectural interest to the room.

Home in Ipswich

Northridge View

Two white rocking chairs sit invitingly along a stone walkway, facing a calm harbor. Reflections of colorful buildings and boats can be seen on the water's surface, framed by a vibrant sky during sunset.

4.97 out of 5 average rating, 87 reviews

Charming waterfront home. Patio, AC, Shops, Dining

A modern kitchen is highlighted by a large central island with seating for four. White cabinetry contrasts with a tiled backsplash in soft green tones. A sleek range hood is positioned above a gas cooktop, while steps lead to the upper level to the right.

4.98 out of 5 average rating, 51 reviews

Harbor House with Ocean Views

A bright living room is showcased with a light-colored sectional sofa and a wooden coffee table. Natural light filters through the windows, illuminating decor elements including books and vases. A mounted TV is positioned on a wall adjacent to a detailed bookshelf.

4.87 out of 5 average rating, 83 reviews

Beach Life Bliss - steps to the beach

A screened-in porch features a comfortable seating arrangement, with a black wicker sofa and red cushions. Potted ferns and a decorative nest adorn the walls. Natural light filters through the lattice, and a patterned rug adds a touch of color to the space.

4.89 out of 5 average rating, 66 reviews

A Breezy Cottage at Back Beach

A custom chef’s kitchen is presented with white cabinetry and a large island featuring seating for three. Natural light fills the space through oversized windows, highlighting exposed wooden beams on the ceiling. A stainless steel refrigerator and dishwasher complement the modern design.

4.97 out of 5 average rating, 34 reviews

Breathtaking Retreat - Walk to Beach & Downtown

5 out of 5 average rating, 17 reviews

A spacious living area is designed with large windows providing expansive views of the ocean. A comfortable white sofa faces a wooden coffee table, complemented by a cozy throw. Natural light fills the room, accentuating the warm wooden floors and tasteful decor.

Home in Nahant

Sea Forever - Oceanfront Home in Nahant!

5 out of 5 average rating, 37 reviews

A bright master suite features French doors that open to a private balcony, offering views of the surrounding landscape. Two chairs sit beside a small table, creating a cozy conversation area, while natural light fills the space from multiple windows.

Home in Ipswich

The Nest at The Neck

Private house rentals

A living room features a modern teal sectional sofa complemented by a wooden coffee table on a light area rug. Bright windows allow natural light to fill the space, while a ceiling fan adds comfort. Doorways lead to the outside and other areas of the house.

4.93 out of 5 average rating, 40 reviews

2 bedroom in heart of Gloucester

The charming cottage exterior features a welcoming porch with two rocking chairs and lush greenery surrounding it. The light-colored facade is complemented by dark windows and a pitched roof, creating a cozy, inviting appearance. A manicured lawn enhances the overall setting.

5 out of 5 average rating, 19 reviews

Chic Coastal Retreat

4.88 out of 5 average rating, 26 reviews

An aerial view of a shoreline captures a stretch of sandy beach bordered by rolling waves. A cluster of houses is visible along the beach, with one cottage highlighted. The sky displays soft clouds in warm hues, suggesting a serene atmosphere.

Home in Plum Island

"Shooting Star" | Beach Front | Pet Friendly

4.95 out of 5 average rating, 41 reviews

A spacious deck area is shown, featuring comfortable seating arrangements in various bright colors. Umbrellas provide shade over the seating. A sandy area leads up to the beach, with a white fence enclosing the yard and neighboring houses visible in the background.

Home in Salisbury

Adorable spacious renovated private home on beach

5 out of 5 average rating, 23 reviews

Home in Salem

Cozy Salem cottage w/ private driveway & backyard

5 out of 5 average rating, 53 reviews

The exterior of a newly renovated, two-story blue house is displayed, featuring white trim and multiple windows. Greenery surrounds the entrance, while a manicured garden adds a natural touch. The background shows additional residences, indicating a residential neighborhood setting.

Home in Newburyport

Quaint House w/parking in the Heart of Downtown

A panoramic view reveals the tranquil ocean, with soft waves lapping against the shore. Green trees and distant sandy areas are visible, enhancing the natural scenery. Several rooftops in the foreground provide a sense of elevation and perspective towards the coastline.

4.98 out of 5 average rating, 94 reviews

Ocean views! Welcome to Sea Breeze!

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. White cabinetry offers ample storage, while a large window allows natural light to illuminate the countertop. A sink is positioned near the window, enhancing functionality in the space.