Holiday rentals in Westport

Place to stay in Westport

4.9 out of 5 average rating, 114 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

4.95 out of 5 average rating, 293 reviews

Cabin in Westport

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!

4.78 out of 5 average rating, 243 reviews

Kayak in the Westport River!

Great place to stay when in town for graduations, weddings (very close to Bittersweet Farms and UMass) or just to escape and relax!! Enjoy yourself in my private, bright and cozy little house right on the river! Back deck with gas grill and great coffee, donuts and ice-cream across the street. Brand new kitchen too!! *Note, no excessive noise, parties or gatherings are allowed. Only those approved to stay in the house are permitted. Guests in violation will be asked to leave immediately.

4.77 out of 5 average rating, 109 reviews

Flat in Fairhaven

Main Street on the Park

Welcome to Main Street on the Park! The morning sun will greet you in the bright apartment in our big white house with a yellow front door. Perfect for a romantic getaway or a convenient place to stay if you are in the area for business. A large fenced yard abuts a public park complete with tennis courts, track and walking trail. Explore our small town with a big history, visit its historic buildings, great restaurants and unique shops. The location is convenient to all of the South Coast.

4.9 out of 5 average rating, 105 reviews

Cottage in Westport

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.

5 out of 5 average rating, 4 reviews

Guest house in Westport

The Swift's Nest

Visiting the Farm Coast? Why not stay on a Farm! The Swift's Nest is a guest house located on our working farm and garden. The studio apartment is private and accessed by a farm lane that will take you past our apiary, orchard and wildflower gardens. Located above our honey room, this generous studio enjoys exceptional views. Distant winter views of the Westport River are replaced by a bright pastoral of wildflowers, hayfields, and forests in the summer. Come enjoy and relax.

5 out of 5 average rating, 127 reviews

Tiny home in Westport

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.

4.88 out of 5 average rating, 286 reviews

Loft in Westport

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.

4.89 out of 5 average rating, 136 reviews

Guest house in Dartmouth

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.

4.96 out of 5 average rating, 321 reviews

Flat in Little Compton

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.

4.85 out of 5 average rating, 109 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.

4.94 out of 5 average rating, 16 reviews

Cottage in Westport

Cottage on Watuppa Pond

Experience a peaceful escape in a picturesque setting, this property offers a perfect blend of modern comforts and natural beauty, making it an ideal destination for your next getaway. Step outside and be enchanted by the nature surrounding the property. The large backyard offers a peaceful retreat, ideal for morning coffee, afternoon relaxation, or stargazing at night.

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Other great holiday rentals in Westport

5 out of 5 average rating, 38 reviews

Home in South Dartmouth

Mermaid’s Lair. Padanaram Village, So. Dartmouth

AidenRating, 5 stars1 week ago

We had the absolute pleasure of staying at Tracy’s beautiful home after our wedding, and it was the perfect way to end our unforgettable day. The peaceful, waterfront setting was calming and romantic, and Tracy went above and beyond to make us feel special with a thoughtful bottle of wine, snacks, drinks, and a personalized congratulatory card. The home was spotless, cozy, and full of charm. Every detail felt just right. We are beyond grateful to Tracy for helping make our wedding night even more magical. If you’re looking for a peaceful, romantic escape with a host who genuinely cares about her guests, look no further. This place isn’t just a stay, it’s a memory you’ll cherish forever. Thank you, Tracy!

4.67 out of 5 average rating, 21 reviews

11 Operation

BeckyRating, 5 stars6 months ago

This is a beautiful, old home that has been remodeled nicely. The kitchen amenities are solid. We hosted a Thanksgiving dinner here for my local family and it was absolutely perfect for the occasion. I saw the previous review about heat issues and mold, but we didn't encounter any of those problems. The heat worked very well on the main floor. It was a little chilly in the upstairs bedroom, but nothing that a portable wall heater couldn't take care of. The beds were super comfortable and everything was very clean. The layout of the bedrooms is a little awkward, but nothing insurmountable. There are some hard-to-navigate stairs that lead to the upstairs bedroom that would be impossible for the very old to navigate, but my teenage kids did just fine getting up there. The host was incredibly responsive and even had warm, homemade sourdough bread waiting for us! John is a wonderful host and this home is a true find.

5 out of 5 average rating, 9 reviews

Barn in Adamsville

Charming country converted barn near RI/MA ocean

MargaretRating, 5 stars2 weeks ago

We had a relaxing stay at Christopher’s bucolic “tree house” cottage. The grounds were lovely and in close proximity to many nature walks and amenities. Our hosts couldn’t have been nicer!

4.88 out of 5 average rating, 121 reviews

Home in Little Compton

John Dyer Loft by Kristin & Sakonnet Farm & Stays

MadeleineRating, 5 stars5 months ago

It was a great space. We rented the apartment for the Christmas holiday, for my daughter and her partner and Kristen was very accommodating. It is near to our home so it worked great. It was a homey place for them to spend the holiday.

4.97 out of 5 average rating, 30 reviews

Westport Waterfront Retreat

CherylRating, 5 stars3 weeks ago

What a beautiful house and location! It had plenty of room for our families. We visited with my family of 4 and my brother’s family of 3. We grew up in Westport and was in town visiting family. The house had everything we needed to be able to hang out and cook meals together. The house was spotless and king beds were very comfortable.

Place to stay in Dartmouth

4.86 out of 5 average rating, 37 reviews

No Egrets Haven-Oceanfront Retreat

KellyRating, 5 stars4 weeks ago

We had a lovely stay here for a bachelorette weekend with a group of 10. The location was absolutely gorgeous, and the views from the deck were a dream—perfect for morning coffee or evening cocktails. The home was spotless, beautifully appointed, and thoughtfully decorated with coastal charm. The kitchen was a standout—spacious and well-stocked, ideal for cooking and gathering as a group. The bedrooms and beds were incredibly comfortable, and the gardens around the property were stunning and well-maintained. Would absolutely recommend this home for a special group getaway!