House holiday rentals in Westerly
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Top-rated house rentals in Westerly
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Westerly
House rentals with a pool
Home in Shelter Island
4.97 out of 5 average rating, 197 reviewsHuge Island Getaway Pool HotTub Walk To Beach
5–12 Dec
Home in Sag Harbor
4.89 out of 5 average rating, 166 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
7–14 May
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
5–12 Dec
Home in Sag Harbor
4.94 out of 5 average rating, 102 reviewsSag Harbor Village Cottage with Pool
11–18 Jun
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
31 Dec – 7 Jan
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
6–13 Dec
Home in Water Mill
4.91 out of 5 average rating, 110 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
1–8 Jan
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
29 Oct – 5 Nov
Weekly house rentals
Home in Coventry
4.85 out of 5 average rating, 110 reviewsAwesome 3 bed vacation lake house. Great location!
1–8 Nov
Home in Lyme
4.97 out of 5 average rating, 190 reviews“The Answer” Tidal River-Kayaks Fire pit Fireplace
Home in Westerly
5.0 out of 5 average rating, 36 reviewsHome Away Cottage
6–13 Oct
Home in Westerly
4.99 out of 5 average rating, 67 reviewsCheerful Cozy Colonial
18–25 Jan
Home in Stonington
4.94 out of 5 average rating, 35 reviewsCharming 1870s Home Near Beaches and Casinos
13–20 Jan
Home in Stonington
4.98 out of 5 average rating, 55 reviewsA Well Appointed Pad…Flexi-Stay Options
5–12 Apr
Home in Westerly
5.0 out of 5 average rating, 18 reviewsNewly renovated cottage! 0.2 mi walk to the beach!
22–29 Sep
Home in Westerly
4.99 out of 5 average rating, 91 reviewsCute and Close to Beaches and Town
11–18 Apr
Private house rentals
Home in Westerly
5.0 out of 5 average rating, 11 reviewsMisquamicut Beach House, 1 Mile From the Ocean!
1–8 Apr
Home in Westerly
4.95 out of 5 average rating, 94 reviewsCharming Dunn’s Corners (Westerly) Cape
22–29 Oct
Home in Haddam
5.0 out of 5 average rating, 78 reviewsCozy Comforts!
20–27 Jan
Home in Westerly
4.97 out of 5 average rating, 36 reviewsPrivate chic waterfront retreat-newly renovated.
2–9 Nov
Home in Stonington
4.98 out of 5 average rating, 64 reviewsUnobstructed water views & huge patio with hot tub
29 Sep – 6 Oct
Home in Westerly
5.0 out of 5 average rating, 11 reviewsPrivate Beach & Salt Pond Access in Shelter Harbor
23–30 Nov
Home in Westerly
5.0 out of 5 average rating, 9 reviewsBeach House Minutes to relaxing by the ocean
10–17 Jan
Home in Westerly
4.87 out of 5 average rating, 54 reviewsElegant Modern 5BR Home:Pool Table, Swim Spa, BBQ
20–27 Apr
Quick stats about house rentals in Westerly
Total rentals
150 properties
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
130 properties are a good fit for families
Total number of reviews
4.1K reviews
Destinations to explore
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