Vacation rentals in Weston

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Weston

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

Guest favorite

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.

Oct 24 – 31

$99 per night
Guest favorite

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.

Aug 18 – 25

$107 per night
Guest favorite

Apartment 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!

Jan 6 – 13

$155 per night

Popular amenities for Weston vacation 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 vacation rentals in Weston

Guest favorite

Guesthouse in Weston

4.96 out of 5 average rating, 24 reviews

Nature Lovers Guesthouse

May 24 – 31

$259 per night
Guest favorite

Guesthouse in Wilton

4.96 out of 5 average rating, 94 reviews

The Cozy Little Cottage

May 2 – 9

$124 per night
Guest favorite

Guesthouse in Wilton

5.0 out of 5 average rating, 21 reviews

The Ciderhouse Cottage - private escape in Wilton

May 23 – 30

$275 per night
Guest favorite

Guest suite in Wilton

4.9 out of 5 average rating, 99 reviews

Serene Pond Views charming private patio…

Aug 19 – 26

$122 per night
Superhost

Home in Fairfield

4.9 out of 5 average rating, 31 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

Sep 7 – 14

$93 per night
Guest favorite

Home in Weston

5.0 out of 5 average rating, 36 reviews

Gorgeous Weston Retreat with Tennis & Hot Tub

May 23 – 30

$897 per night
Guest favorite

Cabin in Redding

4.99 out of 5 average rating, 71 reviews

The Zen Cabin

Feb 28 – Mar 7

$349 per night
Guest favorite

Home in Westport

5.0 out of 5 average rating, 15 reviews

Charming & Spacious New England Family Home

Dec 1 – 8

$385 per night
Guest favorite

Home in Wilton

4.98 out of 5 average rating, 51 reviews

The Yellow House

Aug 8 – 15

$598 per night
Superhost

Home in Redding

4.83 out of 5 average rating, 12 reviews

Meeker Hill House - Charm & Pool

Nov 16 – 23

$657 per night
Guest favorite

Home in Redding

5.0 out of 5 average rating, 32 reviews

Modern Farmhouse in Redding - Walk to Metro North

Dec 6 – 13

$225 per night
Guest favorite

Home in Redding

5.0 out of 5 average rating, 17 reviews

Quiet and Cozy Cottage near NYC with a Pond

Feb 18 – 25

$324 per night

Quick stats about vacation 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

$40 before taxes and fees

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Weston?

    Four-legged friends are welcome in Weston. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Weston?

    Yes! Work meets play with ease at over 40 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Weston have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Weston. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Weston?

    Experience the best of Weston with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Weston have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Weston. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Weston?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with a kitchen, over 30 homes with air conditioning, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Weston have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Weston. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Weston?

    Weston has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Weston have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Weston. Enjoy a tailored experience with all the comforts you desire.

  • Are there Weston vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Weston, available on Airbnb. Make a splash and soak up the sun in style!

Destinations to explore

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