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Holiday Rentals in Wilton

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5 km
46 rentals in Wilton.
Charming Cottage located on Historic Estate 1 Hour from NYC!, holiday rental in Wilton
Charming Cottage located on Historic Estate 1 Hour from NYC!, holiday rental in Wilton
Charming Cottage located on Historic Estate 1 Hour from NYC!, holiday rental in Wilton

Charming Cottage located on Historic Estate 1 Hour from NYC!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Updated Farmhouse Retreat, holiday rental in Wilton
Updated Farmhouse Retreat, holiday rental in Wilton
Updated Farmhouse Retreat, holiday rental in Wilton

Updated Farmhouse Retreat

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Getaway for Thankgiving Holiday - with Fully stocked Chef's Kitchen, holiday rental in Wilton
Getaway for Thankgiving Holiday - with Fully stocked Chef's Kitchen, holiday rental in Wilton
Getaway for Thankgiving Holiday - with Fully stocked Chef's Kitchen, holiday rental in Wilton

Getaway for Thankgiving Holiday - with Fully stocked Chef's Kitchen

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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The following properties within 32 kms of Wilton match all your filters:
Adorable 1-Bedroom Cottage in Weston, CT, holiday rental in Wilton
Adorable 1-Bedroom Cottage in Weston, CT, holiday rental in Wilton
Adorable 1-Bedroom Cottage in Weston, CT, holiday rental in Wilton

Adorable 1-Bedroom Cottage in Weston, CT

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy country cottage in horse country ,private 1 hour toNYC, holiday rental in Wilton
Cozy country cottage in horse country ,private 1 hour toNYC, holiday rental in Wilton
Cozy country cottage in horse country ,private 1 hour toNYC, holiday rental in Wilton

Cozy country cottage in horse country ,private 1 hour toNYC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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European style country chic with pool & privacy!, holiday rental in Wilton
European style country chic with pool & privacy!, holiday rental in Wilton
European style country chic with pool & privacy!, holiday rental in Wilton

European style country chic with pool & privacy!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Apartment in Downtown Westport, holiday rental in Wilton
Historic Apartment in Downtown Westport, holiday rental in Wilton
Historic Apartment in Downtown Westport, holiday rental in Wilton

Historic Apartment in Downtown Westport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Escape to The River Loft, a secluded private riverfront retreat in Weston, CT., holiday rental in Wilton
Escape to The River Loft, a secluded private riverfront retreat in Weston, CT., holiday rental in Wilton
Escape to The River Loft, a secluded private riverfront retreat in Weston, CT., holiday rental in Wilton

Escape to The River Loft, a secluded private riverfront retreat in Weston, CT.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxurious Water Front House -- With large dock!, holiday rental in Wilton
Luxurious Water Front House -- With large dock!, holiday rental in Wilton
Luxurious Water Front House -- With large dock!, holiday rental in Wilton

Luxurious Water Front House -- With large dock!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Apartment with 2 Bedroom 2 Bathrooms inside house, holiday rental in Wilton
Apartment with 2 Bedroom 2 Bathrooms inside house, holiday rental in Wilton
Apartment with 2 Bedroom 2 Bathrooms inside house, holiday rental in Wilton

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., holiday rental in Wilton
Riverfront retreat in the woods of scenic Weston, Connecticut., holiday rental in Wilton
Riverfront retreat in the woods of scenic Weston, Connecticut., holiday rental in Wilton

Riverfront retreat in the woods of scenic Weston, Connecticut.

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Designer In Town Home- walk to train and town, holiday rental in Wilton
Designer In Town Home- walk to train and town, holiday rental in Wilton
Designer In Town Home- walk to train and town, holiday rental in Wilton

Designer In Town Home- walk to train and town

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Weston 4 bed house with swimming pool, holiday rental in Wilton
Stunning Weston 4 bed house with swimming pool, holiday rental in Wilton
Stunning Weston 4 bed house with swimming pool, holiday rental in Wilton

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, holiday rental in Wilton
Feist House - Hot Tub + Beach Retreat in Nature, holiday rental in Wilton
Feist House - Hot Tub + Beach Retreat in Nature, holiday rental in Wilton

Feist House - Hot Tub + Beach Retreat in Nature

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach, holiday rental in Wilton
Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach, holiday rental in Wilton
Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach, holiday rental in Wilton

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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Mid-Century Modern Hilltop Retreat, holiday rental in Wilton
Mid-Century Modern Hilltop Retreat, holiday rental in Wilton
Mid-Century Modern Hilltop Retreat, holiday rental in Wilton

Mid-Century Modern Hilltop Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Monthly Rental-4 Bedroom Colonial in Westport, CT, holiday rental in Wilton
Monthly Rental-4 Bedroom Colonial in Westport, CT, holiday rental in Wilton
Monthly Rental-4 Bedroom Colonial in Westport, CT, holiday rental in Wilton

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, holiday rental in Wilton
Westport: Walk to Town (Really) Private Yard, One Floor, holiday rental in Wilton
Westport: Walk to Town (Really) Private Yard, One Floor, holiday rental in Wilton

Westport: Walk to Town (Really) Private Yard, One Floor

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Walk-To-Town Cozy Colonial with Fireplace!, holiday rental in Wilton
Walk-To-Town Cozy Colonial with Fireplace!, holiday rental in Wilton
Walk-To-Town Cozy Colonial with Fireplace!, holiday rental in Wilton

Walk-To-Town Cozy Colonial with Fireplace!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Family Home, holiday rental in Wilton
Spacious Family Home, holiday rental in Wilton
Spacious Family Home, holiday rental in Wilton

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 in Wilton
Beautiful Westport Historic 4 Bedroom Gem, holiday rental in Wilton
Beautiful Westport Historic 4 Bedroom Gem, holiday rental in Wilton

Beautiful Westport Historic 4 Bedroom Gem

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 2
Match: Sleeps
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Charming Country Getaway on Stillwater Pond, holiday rental in Wilton
Charming Country Getaway on Stillwater Pond, holiday rental in Wilton
Charming Country Getaway on Stillwater Pond, holiday rental in Wilton

Charming Country Getaway on Stillwater Pond

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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New Canaan-Great Fairfield County Location. Walk to Town. Walk to Train, holiday rental in Wilton
New Canaan-Great Fairfield County Location. Walk to Town. Walk to Train, holiday rental in Wilton
New Canaan-Great Fairfield County Location. Walk to Town. Walk to Train, holiday rental in Wilton

New Canaan-Great Fairfield County Location. Walk to Town. Walk to Train

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Westport Summer Estate, holiday rental in Wilton
Westport Summer Estate, holiday rental in Wilton
Westport Summer Estate, holiday rental in Wilton

Westport Summer Estate

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn, holiday rental in Wilton
Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn, holiday rental in Wilton
Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn, holiday rental in Wilton

Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach, holiday rental in Wilton
Modern 4 bed 4.5 bath w hot tub & heated pool close to beach, holiday rental in Wilton
Modern 4 bed 4.5 bath w hot tub & heated pool close to beach, holiday rental in Wilton

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., holiday rental in Wilton
Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., holiday rental in Wilton
Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., holiday rental in Wilton

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 in Wilton
Walk-to-Town New home w/new furnishings, Grill Center & Playset, holiday rental in Wilton
Walk-to-Town New home w/new furnishings, Grill Center & Playset, holiday rental in Wilton

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 in Wilton
Newly renovated summer home in Westport CT private pool & spa, near beach & town, holiday rental in Wilton
Newly renovated summer home in Westport CT private pool & spa, near beach & town, holiday rental in Wilton

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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Private New Canaan Compound, holiday rental in Wilton
Private New Canaan Compound, holiday rental in Wilton
Private New Canaan Compound, holiday rental in Wilton

Private New Canaan Compound

Holiday Rental House
5 bedrooms
8 bathrooms
Sleeps 10
Match: Sleeps
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Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail, holiday rental in Wilton
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail, holiday rental in Wilton
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail, holiday rental in Wilton

Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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July family retreat. Pool, hot-tub, full gym, basketball court, pickelball, holiday rental in Wilton
July family retreat. Pool, hot-tub, full gym, basketball court, pickelball, holiday rental in Wilton
July family retreat. Pool, hot-tub, full gym, basketball court, pickelball, holiday rental in Wilton

July family retreat. Pool, hot-tub, full gym, basketball court, pickelball

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Coastal Estate, 7min to NYC train & beach.  Heated pool & amazing gardens, holiday rental in Wilton
Luxury Coastal Estate, 7min to NYC train & beach.  Heated pool & amazing gardens, holiday rental in Wilton
Luxury Coastal Estate, 7min to NYC train & beach.  Heated pool & amazing gardens, holiday rental in Wilton

Luxury Coastal Estate, 7min to NYC train & beach. Heated pool & amazing gardens

Holiday Rental House
9 bedrooms
8 bathrooms
Sleeps 15
Match: Sleeps
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The Riverside, holiday rental in Wilton
The Riverside, holiday rental in Wilton
The Riverside, holiday rental in Wilton

The Riverside

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Westport Manor with 40 Foot Heated Pool/Spa, holiday rental in Wilton
Westport Manor with 40 Foot Heated Pool/Spa, holiday rental in Wilton
Westport Manor with 40 Foot Heated Pool/Spa, holiday rental in Wilton

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 in Wilton
An oasis in a magnificent & scenic setting in Westport CT, holiday rental in Wilton
An oasis in a magnificent & scenic setting in Westport CT, holiday rental in Wilton

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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Charming 2 Bedroom Cottage in Peaceful New Canaan, holiday rental in Wilton
Charming 2 Bedroom Cottage in Peaceful New Canaan, holiday rental in Wilton
Charming 2 Bedroom Cottage in Peaceful New Canaan, holiday rental in Wilton

Charming 2 Bedroom Cottage in Peaceful New Canaan

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Classic New England Masterpiece in the Heart of Westport, holiday rental in Wilton
Classic New England Masterpiece in the Heart of Westport, holiday rental in Wilton
Classic New England Masterpiece in the Heart of Westport, holiday rental in Wilton

Classic New England Masterpiece in the Heart of Westport

Holiday Rental House
6 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Riverfront Weston Home-1 Hr to NYC, holiday rental in Wilton
Beautiful Riverfront Weston Home-1 Hr to NYC, holiday rental in Wilton
Beautiful Riverfront Weston Home-1 Hr to NYC, holiday rental in Wilton

Beautiful Riverfront Weston Home-1 Hr to NYC

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Waterfall View - 5 Bedroom, holiday rental in Wilton
Stunning Waterfall View - 5 Bedroom, holiday rental in Wilton
Stunning Waterfall View - 5 Bedroom, holiday rental in Wilton

Stunning Waterfall View - 5 Bedroom

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?, holiday rental in Wilton
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?, holiday rental in Wilton
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?, holiday rental in Wilton

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Connecticut Home w/ Grill & Spacious Yard, holiday rental in Wilton
Historic Connecticut Home w/ Grill & Spacious Yard, holiday rental in Wilton
Historic Connecticut Home w/ Grill & Spacious Yard, holiday rental in Wilton

Historic Connecticut Home w/ Grill & Spacious Yard

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Designer 3BR Family Home | Backyard, Patio & Gym, holiday rental in Wilton
Designer 3BR Family Home | Backyard, Patio & Gym, holiday rental in Wilton
Designer 3BR Family Home | Backyard, Patio & Gym, holiday rental in Wilton

Designer 3BR Family Home | Backyard, Patio & Gym

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Westport In-Town Stay, holiday rental in Wilton
Westport In-Town Stay, holiday rental in Wilton
Westport In-Town Stay, holiday rental in Wilton

Westport In-Town Stay

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Mid-Century Pet-Friendly Retreat – Walk to Westport Shops and Beaches, Private, holiday rental in Wilton
Mid-Century Pet-Friendly Retreat – Walk to Westport Shops and Beaches, Private, holiday rental in Wilton
Mid-Century Pet-Friendly Retreat – Walk to Westport Shops and Beaches, Private, holiday rental in Wilton

Mid-Century Pet-Friendly Retreat – Walk to Westport Shops and Beaches, Private

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly., holiday rental in Wilton
Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly., holiday rental in Wilton
Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly., holiday rental in Wilton

Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Showing results 1-46 of 46
Frequently Asked Questions about Wilton