Family-friendly vacation rentals in Westport

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Top-rated family-friendly rentals in Westport

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

The historic home showcases a charming exterior with weathered shingle siding and multiple large windows. A small ornamental tree is planted in the front garden, surrounded by well-maintained flowerbeds with colorful blooms. A stone marker displays the address '513' prominently.

Place to stay in Westport

4.9 out of 5 average rating, 119 reviews

Coastal Retreat with Historical Charm

Planning a visit to Southern New England? The historic home is centrally located near Newport, Providence, Cape Cod and the ferry to Nantucket. Westport is a charming seaside community with a relaxed and peaceful atmosphere. You will enjoy private accommodation in a historic home designed for a luxurious stay. Surrounded by a kaleidoscope of art and design, treat yourself to a king-sized Posturepedic bed enveloped in pressed linen sheets, sumptuous bath, heated floors and walk in rain shower

Guest favorite

The exterior of the historic schoolhouse displays white siding and a gabled roof. Two prominent front doors, labeled 'No 1,' provide entry. The bell tower features a visible bell, and the surrounding landscape includes carefully arranged flower beds and a stone path.

Farm stay in Tiverton

4.95 out of 5 average rating, 238 reviews

4 Corners Schoolhouse No.1 Kristin &Sakonnet Farm

Stay at the renovated Old Tiverton Four Corners Schoolhouse No. 1, a historic gem built in 1800. The exterior mirrors its original schoolhouse facade, while the interior blends modern comforts with historic charm. The home features a gourmet kitchen, cozy living room with a wood-burning fireplace, two bedrooms, and a Whirlpool tub. Located within walking distance of Tiverton Four Corners village, offering unique shops, restaurants, and more. No pets allowed. Ask for your free weekend itinerary!

Superhost

A serene view of the Westport River at dusk features soft pastel hues reflecting on the water. A wooden dock extends into the calm river, framed by gentle grasses in the foreground. The sky transitions from deep blue to warm oranges and yellows as the sun sets.

Cabin in Westport

4.94 out of 5 average rating, 300 reviews

Koselig Cabin on the Farm Coast of New England!

This cabin is full of comforts, convenience, and love. Just miles from Horseneck Beach. It is located under a mile to Buzzards Bay Brewery and Westport Rivers Winery and a 5 minute walk to the quiet little neighborhoods private beach on the East Branch of the Westport River. Koselig embodies feelings of family, friends, warmth, love, coziness, contentment, and comfort. We have a custom area and house guide at the Cabin with everything you need to know to maximize your experience in the area!

Guest favorite

Two colorful kayaks are positioned on a concrete dock, with the calm waters of the bay extending into the distance. The sky above is clear with some soft clouds, reflecting a tranquil outdoor setting.

Cottage in Westport

4.89 out of 5 average rating, 111 reviews

Kayaks and Glimpses of Westport Bay

Stay in a lovely and comfortable cottage with partial views of the bay. The water is just a short walk away past our neighbor with shared access to the water. Enjoy swimming, fishing, or relaxing on the float and soak up the sun. You can also explore the Horseneck Beach, wander the trails, taste the local farms and restaurants, and more. If you want to unwind at the cottage, watch shows on the 65" Samsung Smart TV, fast Wi-Fi, sit on the deck, and flip some burgers on the gas grill.

Top guest favorite

A classic 1890s farmhouse is portrayed, featuring white clapboard siding and dark red shutters. A stone wall borders the property, complemented by surrounding trees and shrubbery. The home's tall windows and chimney add to its traditional charm, with a glimpse of a nearby outbuilding visible in the background.

Home in Westport

4.95 out of 5 average rating, 103 reviews

Land + Sea - a country coastal retreat

Land + Sea is an 1890s farmhouse in the Head of Westport neighborhood, just a few minutes walk to the East Branch of the Westport River. Spend the days kayaking nearby or at nearby beaches, then come back to rinse off in the outdoor shower. Close to Buzzard Bay Brewing, Westport Rivers Winery, farmstands, dairies, cycling loops, galleries/studios and conservation areas. Prepare local foods in the chef's kitchen or on the grill. A comfy pull-out sofa is an option for overnight guests.

Top guest favorite

A cozy living area features a stone fireplace, with a muted flame providing a warm glow. Above, a flat-screen TV is mounted against white shiplap walls, complemented by exposed beams. A dark wood coffee table sits at the center, surrounded by comfortable seating and decorative accents.

Home in New Bedford

4.99 out of 5 average rating, 247 reviews

Historic Cobblestone Carriage House near Downtown

Enjoy a piece of history at this carriage house! Jonathan Bourne owned a mansion along with this home, and his son purchased a whaler, Lagoda, in 1841. The ship is currently displayed at the New Bedford Whaling Museum, which is walking distance; just four/five blocks of downtown New Bedford, where you can also enjoy shopping, great food, entertainment, and the ferry to either Martha’s Vineyard or Nantucket. New 2025 (MBTA) commuter train rail to Boston and more. Check it out!

Top guest favorite

A quaint cottage is blanketed in snow, with a chimney rising from the sloped roof. Nearby, a bare tree stands, its branches weighed down by frost. The scene conveys a tranquil winter landscape, featuring soft white tones and a serene atmosphere.

Tiny home in Westport

5 out of 5 average rating, 135 reviews

Restored blacksmith shop (cottage) on goat farm

Guest cottage on 300-yr old farmstead, now a working goat farm. Open floor plan with Queen bed, decorative FP, loveseat, ++ seating, bistro table/chairs, WiFi, Roku TV w/ prem. channels, a/c & heat, 3 cu. ft. frig, m'wave, coffee maker/tea kettle. NO KITCHEN facilities. Full bath (w/ shower) in attached ell. Bright & cheery, close to barn & goat pen. Shaded outdoor grass patio w/ teak furniture. Orchard (w/ fire pit), pastures, hay fields, stream, walking trails in woods.

Guest favorite

A charming farmhouse is set against a backdrop of autumn foliage, featuring vibrant trees and a cloudy sky. A garden with various plants and flowers is visible in the foreground, adding natural texture to the scene.

Loft in Westport

4.88 out of 5 average rating, 299 reviews

Brithaven Farm

Brithaven Farm is on 28 acres of fields, woods meadows and gardens. We are just 2 miles from East Beach and the Allen's Pond Wildlife Sanctuary. We are completely private from the road and reached by a long laneway through woods which opens up to fields and meadows The rental has 2 decks, one with a large awning with dining table and chairs to lounge and take in the view. There is an open plan living, dining kitchen area with french doors leading to the deck.

Guest favorite

A cozy studio space features sloped ceilings and warm wooden flooring. A spacious bed is dressed in white linens, with accent pillows adding a touch of color. A small kitchenette is visible beside a comfortable chair and a blue rug, offering a relaxed atmosphere.

Guest suite in Dartmouth

4.94 out of 5 average rating, 101 reviews

The Loft @ Beechwood. Private, comfy, coastal!

The Loft is a detached and private studio apartment with a private entrance, beautifully decorated with a coastal decor befitting nearby Padanaram Harbor & Village. The skylights and a 'really, really comfortable bed' will help you relax and enjoy all the area has to offer. Ideal for two guests, but able to accommodate a third, or two children, The Loft is a great home base to explore the local area or the Islands of Cuttyhunk, Martha's Vineyard & Nantucket.

Guest favorite

Two wooden adirondack chairs are positioned on a grassy area, facing a tranquil lake surrounded by trees. Bright yellow daffodils bloom nearby, adding a touch of color to the natural landscape under a clear blue sky.

Guesthouse in Dartmouth

4.89 out of 5 average rating, 146 reviews

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.

Top guest favorite

Aerial view showcases a peaceful coastal neighborhood, with homes set against a backdrop of the ocean. The green lawns and sandy shore create a harmonious landscape. Soft clouds drift above, and the water glistens under natural light, enhancing the serene coastal environment.

Apartment in Little Compton

4.96 out of 5 average rating, 334 reviews

Home by the Sea

Private entrance to the full 1st floor with an ocean view in quiet neighborhood. The apartment features a bedroom with full sized bed, private bathroom, private living room with dining area, gas fireplace, tv and couch. Washer/dryer, refrigerator, microwave, coffee maker, toaster and hot plate included are in the apartment. There also is an additional outdoor H/C shower, private patio and gas grill.

Guest favorite

A stone pathway leads up to the side of a house, bordered by green grass and plants. The two-story structure features a textured wooden exterior and multiple windows. Natural light illuminates the scene under a clear blue sky.

Home in Westport

4.86 out of 5 average rating, 111 reviews

Beach Home – Family Friendly - Solar Powered

1.5 mile to beautiful Horseneck beach. On 2 acres of woods & lawn. Large deck for grilling, outdoor shower, fire pit & large swing set. Spacious & bright layout with cathedral ceilings and hardwood floors . Family friendly private neighborhood. ABSOLUTELY NO PARTIES. IF YOU ARE LOOKING FOR A PLACE TO PARTY, PLEASE GO SOMEWHERE ELSE. WE WILL ASK GUESTS TO LEAVE IF THIS POLICY IS NOT FOLLOWED.