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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.

Superhost
Cottage in Easton
Cozy Modern Country Cottage with Fireplace
Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!
$144 per night
Superhost
Loft in Bridgeport
Cozy Loft in beautiful St. Mary's by the Sea
Renovated cozy loft in beautiful St. Mary's by The Sea in Black Rock. Walking distance to award winning restaurants. Easy access to NYC/New Haven Metro North transit. Perfect for a weekend at the beach. Property includes 1 bed and a 78” sofa. Fully equipped kitchen with all major appliances, WiFi, & large TV. ***Please note that the ceilings are angled so taller guests (over 5’ 8”) might have to bend in certain parts of the loft.
$91 per night
Superhost
Apartment in Redding
Huckleberry Quarters, the Cozy Redding Retreat.
Huckleberry Quarters, totally renovated-2015 studio apartment in secluded, 1918 farm house. Nature lovers retreat within hiking distance of the Saugatuck reservoir. Private entrance with all the amenities; internet, access to laundry. Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.
$132 per night

Stay near Weston's top sights

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

Other great vacation rentals in Weston

Superhost
Guest suite in Fairfield
Adorable private apt w/ W/D in lovely neighborhood
$114 per night
Superhost
Cottage in South Salem
Private cottage in horse country &1 hour from NYC!
$214 per night
Superhost
Apartment in Norwalk
The Seasons Luxe Pad 1 Bedroom | Center of Norwalk
$96 per night
Superhost
Apartment in Brookfield
Peaceful apartment on 3.5 acres w/ Artist studio.
$115 per night
Superhost
Home in Fairfield
Luxurious Barn With New England Charm
$230 per night
Superhost
Guesthouse in Fairfield
Southport, CT across from BEACH
$225 per night
Superhost
Cottage in Weston
The River Loft
$300 per night
Superhost
Apartment in Weston
Relaxing Upscale Studio w/Kitchen in amazin nature
$165 per night
Superhost
Guesthouse in Weston
Weston Guest Cottage with Tennis/Pickleball Court
$227 per night
Superhost
Guesthouse in Weston
Nature Lovers Guesthouse
$259 per night
Superhost
Guesthouse in Wilton
The Cozy Little Cottage
$145 per night
Superhost
Apartment in Westport
Spacious Westport Apt surrounded by nature
$165 per night

Quick stats about vacation rentals in Weston

Total rentals

50 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

860 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 guesthouse rentals in Weston?

    Experience the best of Weston with our guesthouse rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do guesthouse rentals in Weston have wifi?

    Absolutely! We offer over 10 guesthouse 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 free parking, over 30 homes with air conditioning, over 30 homes with wifi, over 30 homes with a kitchen, 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