House holiday rentals in Westport
Find and book unique houses on Airbnb
Top-rated house rentals in Westport
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 Westport
House rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
15–22 Apr
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
17–24 Oct
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
3–10 Feb
Home in Manorville
4.98 out of 5 average rating, 199 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
2–9 Oct
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
23–30 Sep
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
26 Sep – 3 Oct
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
4–11 Feb
Home in Redding
4.83 out of 5 average rating, 12 reviewsMeeker Hill House - Country Escape w/ Heated Pool
11–18 May
Weekly house rentals
Home in Westport
5.0 out of 5 average rating, 4 reviewsWestport:Private Fire Pit Hideaway 5 min to Town
24–31 Aug
Home in Westport
5.0 out of 5 average rating, 19 reviewsCharming & Spacious New England Family Home
4–11 Jan
Home in Westport
4.8 out of 5 average rating, 20 reviewsCustom Westport Home, perfect for families
10–17 Jun
Home in Norwalk
5.0 out of 5 average rating, 34 reviews❤️ Your Silvermine Hideaway, nestled in nature.
20–27 Mar
Home in Westport
5.0 out of 5 average rating, 9 reviewsFarmhouse 1899: Westport, CT
23–30 Sep
Home in Fairfield
5.0 out of 5 average rating, 63 reviewsFairfield Cottage: Cozy retreat near Universities
18–25 Mar
Home in Westport
5.0 out of 5 average rating, 3 reviewsWestport Beach Town Mid-Century Vibe Retreat - Pet
13–20 Jun
Home in Fairfield
4.91 out of 5 average rating, 70 reviewsFairfield 2nd FL Suite w Private Entry & Parking
2–9 Jul
Private house rentals
Home in Redding
5.0 out of 5 average rating, 17 reviewsQuiet and Cozy Cottage near NYC with a Pond
11–18 Dec
Home in Westport
4.93 out of 5 average rating, 14 reviewsBeautiful Brand New Inviting Farmhouse
27 Aug – 3 Sep
Home in Fairfield
5.0 out of 5 average rating, 7 reviewsStillson House - Central Cozy Updated Colonial
11–18 Jun
Home in Milford
5.0 out of 5 average rating, 14 reviewsLuxe Beach House | 3 Bd-King | 4TV | Chef Kitchen
20–27 Sep
Home in Bridgeport
4.97 out of 5 average rating, 29 reviewsCatch some Zzz at Black Rock Harbor
3–10 Mar
Home in Milford
5.0 out of 5 average rating, 43 reviewsWalk to beach & shops. Luxe, designer renovation.
5–12 Mar
Home in Weston
5.0 out of 5 average rating, 36 reviewsGorgeous Weston Retreat with Tennis & Hot Tub
21–28 May
Home in Norwalk
5.0 out of 5 average rating, 3 reviewsGreatly located SoNo 2 bedroom apartment
29 Jan – 5 Feb
Quick stats about house rentals in Westport
Total rentals
90 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
870 reviews
Destinations to explore
- Townhouse rentals New York
- Beach house rentals New York
- Guest house rentals New York
- Lakehouse rentals New York
- Tiny house rentals New York
- House rentals New York
- Guest house rentals United States
- Townhouse rentals United States
- Lighthouse rentals United States
- House rentals United States
- Earth house rentals United States
- Townhouse rentals Manhattan
- House rentals Manhattan
- Guest house rentals Manhattan
- Guest house rentals Brooklyn
- Townhouse rentals Brooklyn
- House rentals Brooklyn
- Guest house rentals Connecticut
- Lakehouse rentals Connecticut
- House rentals Connecticut
- Townhouse rentals Connecticut
- Tiny house rentals Connecticut
- Beach house rentals Connecticut
- Rentals with a patio Westport
- Monthly Rentals Westport
- Fitness-friendly rentals Westport
- Family-friendly rentals Westport
- Rentals with a firepit Westport
- Family-friendly rentals Westport
- Rentals with a fireplace Westport
- Rentals with beach access Westport
- Rentals with outdoor seating Westport
- Rentals with a washing machine and dryer Westport
- Rentals with pools Westport
- Pet-friendly rentals Westport
- House rentals Fairfield County
- Guest house rentals Fairfield County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom