Holiday rentals in Weston

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Weston

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.

24–31 Oct

£109 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

£121 per night
Guest favourite

Flat in Westport

4.94 out of 5 average rating, 112 reviews

Spacious Westport Apt surrounded by nature

Spacious mother-in-law apartment w/ private entrance on the 1st floor of our beautiful home. Windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8-10 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, and wonderful bakeries and restaurants nearby!

6–13 Jan

£159 per night

Popular amenities for Weston holiday rentals

Stay near Weston's top sights

Orem's Diner4 locals recommend
Wire Mill Saloon & Barbeque7 locals recommend
Devil's Den Preserve32 locals recommend
Peter's Weston Market6 locals recommend
Lunch Box6 locals recommend
Milestone6 locals recommend

Other great holiday rentals in Weston

Guest favourite

Guest house in Weston

4.96 out of 5 average rating, 24 reviews

Nature Lovers Guesthouse

24–31 May

£280 per night
Guest favourite

Guest house in Wilton

4.96 out of 5 average rating, 94 reviews

The Cozy Little Cottage

2–9 May

£139 per night
Guest favourite

Guest house in Wilton

5.0 out of 5 average rating, 21 reviews

The Ciderhouse Cottage - private escape in Wilton

23–30 May

£304 per night
Guest favourite

Guest suite in Wilton

4.9 out of 5 average rating, 99 reviews

Serene Pond Views charming private patio…

19–26 Aug

£139 per night
Superhost

Home in Fairfield

4.9 out of 5 average rating, 31 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

7–14 Sept

£103 per night
Guest favourite

Home in Weston

5.0 out of 5 average rating, 36 reviews

Gorgeous Weston Retreat with Tennis & Hot Tub

23–30 May

£947 per night
Guest favourite

Cabin in Redding

4.99 out of 5 average rating, 71 reviews

The Zen Cabin

28 Feb – 7 Mar

£377 per night
Guest favourite

Home in Westport

5.0 out of 5 average rating, 15 reviews

Charming & Spacious New England Family Home

1–8 Dec

£431 per night
Guest favourite

Home in Wilton

4.98 out of 5 average rating, 51 reviews

The Yellow House

8–15 Aug

£656 per night
Superhost

Home in Redding

4.83 out of 5 average rating, 12 reviews

Meeker Hill House - Charm & Pool

16–23 Nov

£709 per night
Guest favourite

Home in Redding

5.0 out of 5 average rating, 32 reviews

Modern Farmhouse in Redding - Walk to Metro North

6–13 Dec

£245 per night
Guest favourite

Home in Redding

5.0 out of 5 average rating, 17 reviews

Quiet and Cozy Cottage near NYC with a Pond

18–25 Feb

£376 per night

Quick stats about holiday rentals in Weston

Total rentals

60 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

970 reviews

Nightly prices starting at

£32 before taxes and fees

Destinations to explore

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