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
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.
7–14 Oct
₹8,225 per night
4.92 out of 5 average rating, 109 reviews
Guest favourite
Home in Fairfield
Luxurious Barn With New England Charm
Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.
23–30 Apr
₹15,906 per night
4.96 out of 5 average rating, 287 reviews
Guest favourite
Cottage in Westport
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.
19–26 Jun
₹24,873 per night
5.0 out of 5 average rating, 56 reviews

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

Superhost
Home in Westport
Westport:Private Fire Pit Hideaway 5 min to Town
6–13 Nov
₹24,458 per night
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Westport
Gorgeous, luxury Cape in Westport!
22–29 Oct
₹34,075 per night
4.91 out of 5 average rating, 35 reviews
Guest favourite
Cottage in Weston
The River Loft
3–10 Jun
₹26,340 per night
4.96 out of 5 average rating, 28 reviews
Guest favourite
Guest house in Wilton
The Cozy Little Cottage
29 Aug – 5 Sep
₹11,461 per night
4.96 out of 5 average rating, 94 reviews
Guest favourite
Flat in Fairfield
Lovely studio apartment, furnished, Southport CT
22–29 Nov
₹13,804 per night
5.0 out of 5 average rating, 23 reviews
Guest favourite
Guest suite in Westport
Westport Paradise! Every Amenity Right Here.
5–12 Aug
₹55,963 per night
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Fairfield
Fairfield Cottage: Cozy Retreat with Chic Decor
29 Jan – 5 Feb
₹19,151 per night
5.0 out of 5 average rating, 54 reviews
Guest favourite
Home in Norwalk
❤️ Your Silvermine Hideaway, nestled in nature.
18–25 Oct
₹14,604 per night
5.0 out of 5 average rating, 33 reviews
Guest favourite
Cottage in Westport
Mill Pond Retreat
22–29 Apr
₹41,454 per night
5.0 out of 5 average rating, 55 reviews
Guest favourite
Flat in Norwalk
Phoenix Engine #1
24 Sep – 1 Oct
₹12,519 per night
5.0 out of 5 average rating, 25 reviews
Guest favourite
Flat in Fairfield
Sunny Fairfield Studio Apartment
3–10 Apr
₹8,217 per night
4.95 out of 5 average rating, 57 reviews
Guest favourite
Home in Fairfield
Fairfield 2nd FL Suite w Private Entry & Parking
22–29 Apr
₹7,663 per night
4.91 out of 5 average rating, 65 reviews

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

2.2T reviews

Destinations to explore

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