Weston Holiday Rentals
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47 rentals in Weston.
Adorable 1-Bedroom Cottage in Weston, CT
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Escape to The River Loft, a secluded private riverfront retreat in Weston, CT.
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Apartment with 2 Bedroom 2 Bathrooms inside house
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Riverfront retreat in the woods of scenic Weston, Connecticut.
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Stunning Weston 4 bed house with swimming pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Feist House - Hot Tub + Beach Retreat in Nature
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Charming Country Getaway on Stillwater Pond
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn
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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach
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Beautiful Riverfront Weston Home-1 Hr to NYC
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Historic Connecticut Home w/ Grill & Spacious Yard
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Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
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The following properties within 20 miles of Weston match all your filters:
Westport Paradise With Every Amenity!
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Brookside Zen Cabin
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Rare--Private Cozy Country-home on Christmas tree farm setting.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage located on Historic Estate 1 Hour from NYC!
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Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Monthly Rental-4 Bedroom Colonial in Westport, CT
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Westport: Walk to Town (Really) Private Yard, One Floor
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Romantic Riverfront Antique Farmhouse in Historic Aspetuck Corners
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Walk-To-Town Cozy Colonial with Fireplace!
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Spacious Family Home
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Westport Historic 4 Bedroom Gem
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 2
Match: Sleeps
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Entire Guest House at Fox Pond Farm with Access to In ground Pool
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Pool & beach vacation in Westport, Connecticut
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Your luxury dream villa! �
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Fabulous private home on desirable street in Westport.
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Historic Designer City Getaway
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Westport Summer Estate
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Summer in Westport, CT! - Renovated, Private, Close to everything!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Updated Farmhouse Retreat
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Connecticut Estate - Now available July 9-23rd 2023
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Getaway for Thankgiving Holiday - with Fully stocked Chef's Kitchen
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Private Luxury Stay in Expansive Home & Property
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Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Walk-to-Town New home w/new furnishings, Grill Center & Playset
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Newly renovated summer home in Westport CT private pool & spa, near beach & town
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Summer estate close to NY, NJ, MA w heated pool sleeps 16+
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Luxury Coastal Estate, 7min to NYC train & beach. Heated pool & amazing gardens
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Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.
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Stunning Waterfall View - 5 Bedroom
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Stay 3 Nights or Longer Until January 31 and Get 15% Off
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Westport Manor with 40 Foot Heated Pool/Spa
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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An oasis in a magnificent & scenic setting in Westport CT
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Cheerful 6-Bedroom Villa with Pool and Tennis Courts near the beach!
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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Westport In-Town Stay
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Classic New England Masterpiece in the Heart of Westport
Holiday Rental House
6 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-47 of 47
Frequently Asked Questions about Weston
- Yes, here are some popular holiday rentals in Weston that have a pool:
- Adorable 1-Bedroom Cottage in Weston, CT
- A private room for any traveler
- Escape to The River Loft, a secluded private riverfront retreat in Weston, CT.
- Yes, here are some popular holiday rentals in Weston that have internet access:
- Adorable 1-Bedroom Cottage in Weston, CT
- A private room for any traveler
- Escape to The River Loft, a secluded private riverfront retreat in Weston, CT.
- Some of the most popular kid friendly rentals in Weston are:
- Adorable 1-Bedroom Cottage in Weston, CT
- A private room for any traveler
- Escape to The River Loft, a secluded private riverfront retreat in Weston, CT.
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