House holiday rentals in Westerly

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Popular amenities for house rentals in Westerly

House rentals with a pool

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 197 reviews

Huge Island Getaway Pool HotTub Walk To Beach

5–12 Dec

€ 854 per night
Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

7–14 May

€ 614 per night
Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

5–12 Dec

€ 727 per night
Guest favourite

Home in Sag Harbor

4.94 out of 5 average rating, 102 reviews

Sag Harbor Village Cottage with Pool

11–18 Jun

€ 857 per night
Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

31 Dec – 7 Jan

€ 895 per night
Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

6–13 Dec

€ 522 per night
Guest favourite

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

1–8 Jan

€ 1,071 per night
Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

29 Oct – 5 Nov

€ 846 per night

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