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Weston Holiday Rentals

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49 rentals in Weston.
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Interior Designer's Enchanting And Bucolic Home, holiday rental in Weston

Interior Designer's Enchanting And Bucolic Home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Modern Home Near NYC, holiday rental in Weston

Spectacular Modern Home Near NYC

5 bedrooms
4 bathrooms
Sleeps 8
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Elegant Country Estate with Equestrian Farm, holiday rental in Weston

Elegant Country Estate with Equestrian Farm

6 bedrooms
4 bathrooms
Sleeps 12
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Lakeside Modern Farmhouse/Craftsman Chalet, holiday rental in Weston

Lakeside Modern Farmhouse/Craftsman Chalet

4 bedrooms
4 bathrooms
Sleeps 8
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Lakefront home with private dock, kayaks,  and paddleboard.  Boat rentals nearby, holiday rental in Weston

Lakefront home with private dock, kayaks, and paddleboard. Boat rentals nearby

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private 3.5 acre estate  Zen House /Historic mid century modern  / lap pool, holiday rental in Weston

Private 3.5 acre estate Zen House /Historic mid century modern / lap pool

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, holiday rental in Weston

FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Retreat in the Country only 1 hour from NYC, holiday rental in Weston

Luxurious Retreat in the Country only 1 hour from NYC

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxe CT Country Home w/ Hi-end WiFi for WFH & School, holiday rental in Weston

Luxe CT Country Home w/ Hi-end WiFi for WFH & School

6 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Charming Cottage By The Sea on Fairfield Beach, holiday rental in Weston

Charming Cottage By The Sea on Fairfield Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS, holiday rental in Weston

Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Waterfront Lake House with Amazing Views, holiday rental in Weston

Stunning Waterfront Lake House with Amazing Views

3 bedrooms
2 bathrooms
Sleeps 7
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Entire Guest House at Fox Pond Farm with Access to In ground Pool, holiday rental in Weston

Entire Guest House at Fox Pond Farm with Access to In ground Pool

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC, holiday rental in Weston

Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC

4 bedrooms
3 bathrooms
Sleeps 12
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Elegant Beachfront, beautiful views. Come  enjoy!, holiday rental in Weston

Elegant Beachfront, beautiful views. Come enjoy!

5 bedrooms
3 bathrooms
Sleeps 10
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5-Br 3-bath Skylit Home on 3 Forested Acres, holiday rental in Weston

5-Br 3-bath Skylit Home on 3 Forested Acres

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Charming Cottage located on Historic Estate 1 Hour from NYC!, holiday rental in Weston

Charming Cottage located on Historic Estate 1 Hour from NYC!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy the serenity of the countryside at Pleasant Valley Trails - Home & Acres, holiday rental in Weston

Enjoy the serenity of the countryside at Pleasant Valley Trails - Home & Acres

2 bedrooms
1 bathroom
Sleeps 4
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Secluded cottage on cul de sac in Rowayton., holiday rental in Weston

Secluded cottage on cul de sac in Rowayton.

2 bedrooms
1 bathroom
Sleeps 4
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Beautiful Home for Your Family Vacation, holiday rental in Weston

Beautiful Home for Your Family Vacation

7 bedrooms
6 bathrooms
Sleeps 12
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Cozy Cottage in Westport, CT (charming & pristine in fabulous location), holiday rental in Weston

Cozy Cottage in Westport, CT (charming & pristine in fabulous location)

2 bedrooms
2 bathrooms
Sleeps 6
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Serene Connecticut Retreat - Luxury 2 bedroom apt, holiday rental in Weston

Serene Connecticut Retreat - Luxury 2 bedroom apt

2 bedrooms
2 bathrooms
Sleeps 4
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North Stamford Guest House, holiday rental in Weston

North Stamford Guest House

2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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1/2 block to Compo Beach on Long Island Sound!, holiday rental in Weston

1/2 block to Compo Beach on Long Island Sound!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern Waterfront Home  * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY, holiday rental in Weston

Modern Waterfront Home * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Mill Pond Retreat, holiday rental in Weston

Mill Pond Retreat

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Westport 'Gold Coast' across from Southport beach, holiday rental in Weston

Westport 'Gold Coast' across from Southport beach

1 bedroom
1 bathroom
Sleeps 3
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Luxury Executive Estate 1 Hr from New York City, holiday rental in Weston

Luxury Executive Estate 1 Hr from New York City

6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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New modern house near the water (WESTPORT RESIDENTS ONLY), holiday rental in Weston

New modern house near the water (WESTPORT RESIDENTS ONLY)

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A New England Jewel with Scenic Beauty, holiday rental in Weston

A New England Jewel with Scenic Beauty

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Updated Farmhouse Retreat, holiday rental in Weston

Updated Farmhouse Retreat

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Studio Cottage on working Horse Farm/ SwimSpa, holiday rental in Weston

Studio Cottage on working Horse Farm/ SwimSpa

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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One of a Kind Cotswold Summer Retreat on 18 Secluded Acres, holiday rental in Weston

One of a Kind Cotswold Summer Retreat on 18 Secluded Acres

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Suburban Getaway. Heated Pool. NO PARTIES., holiday rental in Weston

Suburban Getaway. Heated Pool. NO PARTIES.

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Sophisticated Country Living, holiday rental in Weston

Sophisticated Country Living

4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Nature Lovers Perfect Location, an hour from Manhattan, holiday rental in Weston

Nature Lovers Perfect Location, an hour from Manhattan

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Fine Waterfront Private Home, In Park-like seaing, holiday rental in Weston

A Fine Waterfront Private Home, In Park-like seaing

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Emerald's Farm, holiday rental in Weston

Emerald's Farm

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate, holiday rental in Weston

Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Comfy and Stylish Harbor Point Studio, holiday rental in Weston

Comfy and Stylish Harbor Point Studio

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Newly listed Property, Home Away from Home, Close to restaurants and local beach, holiday rental in Weston

Newly listed Property, Home Away from Home, Close to restaurants and local beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Live/work loft with view and exposed brick, holiday rental in Weston

Live/work loft with view and exposed brick

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Estate Large Private Pool, holiday rental in Weston

Private Estate Large Private Pool

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely River view property, holiday rental in Weston

Lovely River view property

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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NEW! Luxury Forest Escape w/ Creek On-Site + Deck!, holiday rental in Weston

NEW! Luxury Forest Escape w/ Creek On-Site + Deck!

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Comtemporary 1Bdr w/ Queen Bed + Free Wifi, holiday rental in Weston

Comtemporary 1Bdr w/ Queen Bed + Free Wifi

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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New Stylish Beach Home near Stamford Downtown/Cove Beach/ 40 min to NYC �, holiday rental in Weston

New Stylish Beach Home near Stamford Downtown/Cove Beach/ 40 min to NYC �

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Convenient 3 Story Home In The Heart Of Stamford, holiday rental in Weston

Convenient 3 Story Home In The Heart Of Stamford

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Picturesque South Salem Home on Lake w/ Pool!, holiday rental in Weston

NEW! Picturesque South Salem Home on Lake w/ Pool!

1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps
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The West Lane Inn - Queen Room, holiday rental in Weston

The West Lane Inn - Queen Room

1 bedroom
1 bathroom
Sleeps 1
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