Holiday rentals in Westport

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Top-rated holiday rentals in Westport

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

Guest favourite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

25 Oct – 1 Nov

€ 127 per night
Guest favourite

Cottage in Westport

5.0 out of 5 average rating, 55 reviews

Wild Rose Cottage (Westport, CT)

Luxurious newly-renovated Cottage in prime location in Westport's historic district. Studio with queen-sized bed, kitchen (w/fridge, dishwasher, stove, oven, toaster, Keurig), full bathroom, A/C, fireplace, W&D, TV, WiFi (w/Amazon Fire Stick). Parking for one car. Back-up generator. Within stone's throw of Hudson Malone, Outpost Pizza, Merritt Country Store, Coffee An' Donut Shop and Grapevine liquor store. Just a short stroll on the sidewalk to downtown Main Street's shops and restaurants.

30 Jun – 7 Jul

€ 372 per night
Guest favourite

Guest suite in Fairfield

4.93 out of 5 average rating, 107 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

18–25 Aug

€ 141 per night

Popular amenities for Westport holiday rentals

Stay near Westport's top sights

Whole Foods Market22 locals recommend
Trader Joe's62 locals recommend
bartaco71 locals recommend
Shake Shack6 locals recommend
Black Duck Cafe13 locals recommend
Bow Tie Cinema Royale 66 locals recommend

Other great holiday rentals in Westport

Guest favourite

Home in Westport

5.0 out of 5 average rating, 15 reviews

Charming & Spacious New England Family Home

1–8 Dec

€ 504 per night
Guest favourite

Home in Westport

4.92 out of 5 average rating, 36 reviews

Gorgeous, luxury Cape in Westport!

26 Aug – 2 Sep

€ 535 per night
Guest favourite

Flat in Fairfield

5.0 out of 5 average rating, 50 reviews

Bright, private 1,000 sq. ft. 1-Bedroom Apartment

30 Sep – 7 Oct

€ 165 per night
Guest favourite

Home in Westport

5.0 out of 5 average rating, 6 reviews

Farmhouse 1899: Westport, CT

4–11 Apr

€ 759 per night
Guest favourite

Cottage in Weston

4.97 out of 5 average rating, 29 reviews

The River Loft

27 Jun – 4 Jul

€ 402 per night
Superhost

Home in Westport

5.0 out of 5 average rating, 3 reviews

Westport:Private Fire Pit Hideaway 5 min to Town

12–19 Oct

€ 506 per night
Superhost

Home in Fairfield

4.9 out of 5 average rating, 31 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

15–22 Aug

€ 120 per night
Guest favourite

Guest suite in Westport

5.0 out of 5 average rating, 47 reviews

Westport Paradise! Every Amenity Right Here.

21–28 Jul

€ 818 per night
Guest favourite

Apartment in Norwalk

4.94 out of 5 average rating, 18 reviews

*New Studio in the heart of Downtown Norwalk*

14–21 Sep

€ 118 per night
Guest favourite

Home in Fairfield

4.91 out of 5 average rating, 65 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

7–14 May

€ 127 per night
Guest favourite

Flat in Norwalk

5.0 out of 5 average rating, 25 reviews

Phoenix Engine #1

6–13 Aug

€ 186 per night
Guest favourite

Flat in Fairfield

4.95 out of 5 average rating, 58 reviews

Sunny Fairfield Studio Apartment

21–28 Apr

€ 133 per night

Quick stats about holiday rentals in Westport

Total rentals

120 properties

Rentals with dedicated workspaces

70 properties have a dedicated workspace

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

90 properties are a good fit for families

Total number of reviews

2.2K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Fairfield County
  5. Westport