House holiday rentals in Gloucester

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

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.

4.92 out of 5 average rating, 315 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, 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).

4.97 out of 5 average rating, 111 reviews

The exterior of a colonial-style house is presented, featuring a symmetrical façade with a front porch, white railing, and wide steps leading to the entrance. A well-manicured lawn and garden flank the pathway, which guides toward the door. The vibrant greenery complements the home.

Home in Haverhill

Charming 4-Bedroom Colonial

Welcome to this charming colonial nestled within the tranquil suburban Bradford section of Haverhill, Massachusetts. This inviting four-bedroom, 2.5-bath residence offers a serene retreat for those seeking a comfortable and spacious accommodation. This home is perfect for you and your family looking to enjoy your time spent in the awesome private outdoor space near the fire-pit or indoors enjoying a wonderful home cook meal at the dining table gathered around by your love ones.

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!

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.

4.96 out of 5 average rating, 176 reviews

A dining area is showcased with a rustic wooden table surrounded by four chairs and a bench. An arrangement of circular placemats lies on the table. Natural light enters through a window, illuminating the wooden floor and a potted plant sits on the table.

Home in Salem

Beautiful very spacious historical house in Salem

The whole group will enjoy easy access to everything from this centrally located place. A few minutes walk to a multitude of great restaurants, shops, galleries, the witch house, ghost and witch tours, trolley tours, Salem ferry, Pickering wharf, Salem witch museum, witch dungeon museum and a few minutes drive to Salem Willows and the house of the seven gables. All three bedrooms that are on the second floor will have AC units from mid June till September.

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, 103 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, 21 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!

4.97 out of 5 average rating, 58 reviews

A spacious bedroom is presented, featuring a dark wooden bed frame with a light-colored bedding set. Two nightstands with lamps are positioned on either side. Natural light enters through three windows, complementing the warm tones of the wooden floor and subtle wall color.

Home in Kittery

Fantastic Kittery Home with Pool

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

Weekly house rentals

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

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, 84 reviews

Beach Life Bliss - steps to the beach

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 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

4.96 out of 5 average rating, 81 reviews

Newly Renovated Ocean Escape

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, 28 reviews

William Haskell House First Period Colonial Home

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

5 out of 5 average rating, 22 reviews

Gather @ Ocean - Home Sleeps 14 w/ 3.5 baths

Private house rentals

An aerial view captures the charming town of Rockport, MA, showcasing a picturesque harbor filled with boats, seaside buildings, and lush green hills in the background. The coastline is dotted with sandy beaches, while the vibrant community is framed by serene waters, illustrating the coastal allure.

5 out of 5 average rating, 8 reviews

Cottage/Loft Combo!|Deck|Sleeps 7|2 Parking Spaces

5 out of 5 average rating, 13 reviews

Parsons at Stage Fort

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, 89 reviews

Charming waterfront home. Patio, AC, Shops, Dining

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!

5 out of 5 average rating, 8 reviews

Home in Salem

Salem 2BR | Near Downtown | Parking | Yard & Grill

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

The living area features a blue sofa along with a stylish coffee table atop a colorful area rug. A fireplace is set against a decorative stone wall, and a large television is mounted above it. Dining space is visible in the background, along with bright natural light from the windows.

5 out of 5 average rating, 13 reviews

Lobster Trap: Beauport, Pavilion Beach, Downtown

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.