House holiday rentals in Gloucester

4.99 out of 5 average rating, 178 reviews

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.

The image features a serene marina scene under a clear blue sky, with various boats docked along the water. Towering trees and greenery frame the view, while the gentle architecture of nearby buildings adds to the coastal landscape.

4.99 out of 5 average rating, 212 reviews

Rocky Neck Retreat

.Relaxing private location .4 beds 2 baths with full kitchen/pans/Dishwasher/Wash/Dryer.Renovated organic design integrates historic architecture with modern touches.If you come for hikes, beach/music/food scene, you will enjoy the Rocky Neck District .The unique home has 4 bedrooms /4 Queen Beds. Speedy WIFI .Parking is up a steep narrow drive . NO trucks or Large SUVs. 2 cars max. Note* Kitchen and LR are upstairs.There are stairs. Contact owner for questions re:parking or limited mobility.

The exterior of the 1767 Tuck House is shown, featuring a spacious two-story structure with white siding and black shutters. A welcoming teal door is framed by decorative wall sconces. Lush hydrangea bushes bloom in front, complementing the landscaped yard and stone pathway leading to the entrance.

4.98 out of 5 average rating, 109 reviews

Walk to Beach and Town at Historic Luxury Home

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.

A spacious living area features large windows overlooking the water. A gray sofa and a blue armchair provide comfortable seating, while a wooden coffee table sits in front. A dining table with white chairs is positioned nearby, creating an inviting space for relaxation and meals.

4.96 out of 5 average rating, 140 reviews

Views over Lobster Cove! Book spring/summer now

Booking spring and summer. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Large living/dining/kitchen area. Comfy new mattresses, 100% cotton sheets,sound machines. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door. Parking for one car

Superhost

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

4.81 out of 5 average rating, 216 reviews

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, 175 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.

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, 146 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, 348 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.

5 out of 5 average rating, 169 reviews

A welcoming living area showcases a large screen displaying Netflix. Two brown armchairs with throw pillows are positioned beside a modern coffee table. A cozy fireplace adds warmth, while soft gray and blue tones create a relaxing atmosphere. Natural light filters through the windows.

Home in Kittery Point

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

4.93 out of 5 average rating, 180 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, 353 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.

A cozy family room is filled with natural light from multiple large windows, offering views of the outside. A comfortable gray sofa and two white chairs are arranged around a glass coffee table. Decorative pillows and a fresh flower arrangement enhance the inviting setting.

4.96 out of 5 average rating, 101 reviews

Pleasant Place

Pleasant Place is a spacious, clean and centrally located spot to spend time with your family and friends. It has two bedrooms, two full bathrooms and a pull out couch. Sun soaked in natural light, it boasts a newly renovated kitchen, granite island, large dining room and a charming family room with views of the Rockport harbor. Walk downtown, to the beach, or drive around town and take advantage of your own parking spot in the busy summer.

Popular amenities for house rentals in Gloucester

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious exterior view of a charming Georgian Colonial house surrounded by lush landscaping. A gravel driveway leads to a two-car garage. The vibrant green lawn is complemented by a stone path and mature trees, creating a welcoming atmosphere.

4.83 out of 5 average rating, 24 reviews

Mansion in Gloucester with Pool

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

4.95 out of 5 average rating, 20 reviews

An aerial view captures a coastal community along the shoreline, with various residential structures and green spaces visible. The nearby beach stretches along the horizon, while a swimming pool is positioned within a central complex, indicated by a star. The landscape is bright and open.

Home in Hampton

Beach Getaway Minutes from the Ocean!

Home in Lakeside Marblehead

A cozy living area is highlighted by a light grey sofa adorned with soft pillows in neutral tones. A round, woven coffee table sits at the center, accompanied by decorative accents. Two lamps provide soft lighting, complemented by exposed wooden beams overhead.

4.93 out of 5 average rating, 41 reviews

Pet-friendly 4-Bed Home w/Pool, Nature Trails

4.97 out of 5 average rating, 32 reviews

An open area is framed by wooden fencing, leading to a natural landscape filled with trees transitioning from winter. The foreground features low shrubs and a rock arrangement, while the background displays a mix of evergreens and deciduous trees against a cloudy sky.

Home in Candia

Amazing House, Peaceful Shangri-La w/Pool &Hot-Tub

5 out of 5 average rating, 15 reviews

Home in Bedford

Bauhaus Retreat in Nature Preserve w/ Pool

4.97 out of 5 average rating, 108 reviews

Home in Weston

Spacious vacation unit in premium suburban town

Weekly house rentals

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

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, 52 reviews

Harbor House with Ocean Views

4.98 out of 5 average rating, 40 reviews

A quaint beach cottage is surrounded by a lush garden, featuring blooming flowers and greenery. Stone steps lead to the entrance, which is framed by white railing. Two individuals are seen tending to the garden, adding to the inviting atmosphere of the property.

Home in Annisquam

Annisquam Getaway - Water View+Walk To The 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

4.97 out of 5 average rating, 32 reviews

A prominent black anchor sculpture is positioned in the foreground, marking the Salem Maritime National Historic Site. In the background, several historic buildings are visible, including a brown house, contributing to the scenic waterfront view.

Home in Salem

Entire Historic Home Overlooking Maritime Park

A serene beach scene captures the twilight sky with soft pink and orange hues. The calm water reflects the colors, creating gentle patterns on the wet sand. A distant rock formation is visible near the shoreline, enhancing the natural beauty of the coastal landscape.

4.91 out of 5 average rating, 33 reviews

Gloucester Beach House

An outdoor deck features wooden flooring and comfortable seating arrangements, including a central coffee table. Potted red flowers add a touch of color to the space. Warm light fixtures hang above, enhancing the inviting feel of the area.

5 out of 5 average rating, 77 reviews

Walk to DNTN/Beach/Beauport, Boat Island, New Home

A serene waterfront view captures gentle waves reflecting the soft hues of a sunset. Two sailboats float peacefully in the water, while a rocky shoreline and a stone breakwater are visible in the distance.

4.94 out of 5 average rating, 49 reviews

The Fort Hideaway- top of Bearskin Neck

Private house rentals

A spacious deck is adorned with a round table and four chairs featuring red cushions. In the background, vibrant yellow flowers contrast against the blue ocean, with Thatcher Island's twin lighthouses visible in the distance. The scene captures a serene view of water and natural beauty.

5 out of 5 average rating, 41 reviews

Eden Cove

Superhost

A spacious private deck overlooks the tidal Annisquam River, featuring comfortable outdoor seating with blue cushions. A small table is placed beside the seating area. String lights illuminate the space, enhancing the inviting atmosphere for relaxation while enjoying scenic water views.

4.83 out of 5 average rating, 24 reviews

PVT Waterfront Deck|Firepit|Workspace|Free Parking

An aerial view captures the beautiful curves of Long Beach, framed by gentle waves lapping the sandy shore. Coastal homes line the beach, blending with the lush greenery in the background. The azure ocean extends into the distance, reflecting the serene sky above.

5 out of 5 average rating, 36 reviews

Oceanfront Home Rockport

Superhost

The exterior of the home is shown, featuring a grey wooden facade and a spacious deck. Lush greenery surrounds the base of the house, and large windows offer views into the living areas. The setting conveys a serene atmosphere backed by a blue sky.

4.85 out of 5 average rating, 60 reviews

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

The living area showcases a comfortable black leather sofa and an armchair, positioned on a patterned rug. A ceiling fan provides airflow above, while a dining table with wooden chairs is visible in the background, adjacent to a modern kitchen with dark cabinetry.

4.93 out of 5 average rating, 61 reviews

Brand new home minutes to the ocean

A historic Colonial home is depicted with dark wooden siding and multiple windows. The structure features a central door, surrounded by evenly spaced windows on the front facade. Trees and greenery are visible in the surrounding yard, under a bright blue sky.

5 out of 5 average rating, 27 reviews

William Haskell House First Period Colonial Home

An outdoor seating area features colorful chairs in vibrant hues, surrounding a central fire pit set within a grassy landscape. A pergola draped with greenery stands above, while a multi-story house is visible in the background, enhancing the gathering space.

5 out of 5 average rating, 18 reviews

Lovely home by the sea!

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.