Holiday houses in Westerly

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Top-rated holiday rentals in Westerly

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

Condo in Norwich

4.98 out of 5 average rating, 134 reviews

The Vacay Villa

The Vacay Villa, just minutes away from Mohegan Sun, Foxwoods and The Spa at Norwich Inn, offers so many amenities you won’t even have to leave the grounds. Private balcony, fireplace, two outdoor pools currently open, year-round access to luxurious hot tub and saunas, small workout room, laundry facilities, pub and upscale restaurant allow for a one-of-a-kind stay at an incredibly affordable price. Why spend hundreds to stay at the area casinos when you can stay in your own private villa?

Superhost

Cottage in Fairhaven

4.83 out of 5 average rating, 218 reviews

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

Superhost

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

Cozy Town Cottage - Minutes from EH Town

This charming, historic home is perfect for a young family! The original mudroom with laundry, farm kitchen (no dishwasher), spacious dining and living rooms, two bedrooms and one bathroom welcome you on the main level. Upstairs is a larger bedroom and a second bathroom as part of an open primary suite. Take a half mile, tree-covered walk to town, or stop at the grocery store or restaurants just down the street. Sorry but, absolutely no animals as owner has severe allergy.

Guest favourite

Bungalow in Middletown

4.83 out of 5 average rating, 106 reviews

Ellery Beach Bungalow #43– Walk to Beaches & Bites

The Ellery Beach Bungalows are a collection of 5 coastal cottages, each offering a refined yet relaxed setting for exploring Aquidneck Island. Stroll to nearby cafés, restaurants, and shoreline escapes, or reach Newport’s celebrated dining, boutiques, and historic landmarks in 5 minutes by car. Each bungalow includes its own private patio, ideal for unhurried evenings outdoors, and sits just a 1/4 mile from the beach, placing the island’s best experiences within easy reach.

Guest favourite

Home in Middletown

4.86 out of 5 average rating, 29 reviews

Little Creek Retreat - RIBryan Property

Tranquil location near Pebble Beach, 3rd Beach, and Indian Ave, this 4-bedroom, 3-bath house offers privacy and seclusion on a 9-acre plot. It includes a master suite with an en-suite bathroom. The property is well-suited for families, featuring a hot tub, a fenced-in yard, and extra space available for children under 12. This home combines the comfort of expansive private grounds with the convenience of nearby coastal access, providing a peaceful retreat.

Guest favourite

Houseboat in North Fork

5 out of 5 average rating, 11 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Superhost

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Top Guest favourite

Home in Narragansett

5 out of 5 average rating, 15 reviews

Striped Bass Villa - Beachfront Vacation Home

This cozy 2-bedroom home with a loft accommodates 7 guests, offering a serene oceanfront retreat. Featuring a spacious living room, fully equipped kitchen, and bathroom, it ensures all the comforts of home. Step onto the private deck for stunning ocean and sunset views. Direct beach access is exclusively shared only with neighboring owners and guests.

Top Guest favourite

Home in North Fork

4.98 out of 5 average rating, 179 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Guest favourite

Home in Montauk

4.92 out of 5 average rating, 51 reviews

Montauk Family Gem: HotTub, Pro Kitchen, Fireplace

Escape to your perfect Montauk getaway! Nestled on a secluded, beautifully landscaped lot at the end of a quiet dead-end street, this recently renovated 4-bedroom, 3.5-bathroom beach house offers the ultimate combination of luxury, comfort, and privacy. We are also pet friendly!

Top Guest favourite

Home in Middletown

4.98 out of 5 average rating, 52 reviews

Newly Remodeled Cottage near Newport Beach

Escape to Middletown, RI for beautiful waterviews and sunsets from the front deck of this completely renovated 2 bedroom, 1 bathroom cottage walking distance to beaches. Quiet, family friendly neighborhood where you can bbq in the backyard and enjoy s’mores by the fire pit.

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What guests are saying

11 Drift

4.67 out of 5 average rating, 21 reviews4 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.

Home in Westport

What guests are saying

Lakefront Lovely Cottage

4.83 out of 5 average rating, 47 reviews4 months ago

Brenda place was beautiful with a beautiful view especially when we work up to some light snow on the lake. The layout of the house was ideal for us with the big open living room and great updated kitchen. So many comfortable beds for us to use. Our favorite places were the sun room and dining rooms looking out at the lake, Brenda was was kind and helpful and adding a Christmas tree for us was a beautiful touch . Highly recommend, one of our best for sure, thank you

Cottage in Enfield

What guests are saying

Fairhaven Harbor-Front Gem - Steps From the Water!

4.95 out of 5 average rating, 43 reviews2 weeks ago

I can’t say enough great things about this place. We stayed for a week and it felt like home away from home. Everything was spotless and smelled professionally clean. The cabin house was SO CUTE and spacious. Perfect size for family to visit while we were in town, even with the pups. Lots of kitchen utensils, towels, blankets, you name it. We will definitely book again when we come back to visit family.

Home in Fairhaven

What guests are saying

Private vacation home, close to beach

4.93 out of 5 average rating, 42 reviews6 months ago

We loved our stay in Westbrook! Mia's lovely home exceeded our expectations in terms of decor, furnishings, cleanliness, comfortable beds, and well-stocked kitchen and bath ... all in a quiet and private setting. The house was especially well-situated for us. We had tickets for a special theater performance at Gillette Castle one evening, and then had to be in New Haven on the next day. All were easy drives. And, there are amazing fine dining options nearby. We'll definitely try to book this wonderful place any time we have events in the area. Thank you, Mia, for a magical Autumn weekend in Connecticut!

Home in Westbrook

What guests are saying

Cozy, summer house near Misquamicut beach

5 out of 5 average rating, 8 reviews8 months ago

This was one of the greatest Airbnb stays I have had! This house of very continent do the beach. They have chairs and an umbrella for you so you don’t need to pack them. Also there are so many great beaches near by to pick from. This house is beautiful and was perfect for the girls weekend we had planned. We all highly recommend this place and all want to make it our new yearly tradition to stay here!

Home in Westerly