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Westport Holiday Rentals

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49 rentals in Westport.
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Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS, holiday rental in Westport

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

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1/2 block to Compo Beach on Long Island Sound!, holiday rental in Westport

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

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Less than 1 block to the beach in Westport! Long Term Rentals too., holiday rental in Westport

Less than 1 block to the beach in Westport! Long Term Rentals too.

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern Waterfront Home  * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY, holiday rental in Westport

Modern Waterfront Home * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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New modern house near the water (WESTPORT RESIDENTS ONLY), holiday rental in Westport

New modern house near the water (WESTPORT RESIDENTS ONLY)

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Suburban Getaway. Heated Pool. NO PARTIES., holiday rental in Westport

Suburban Getaway. Heated Pool. NO PARTIES.

5 bedrooms
3 bathrooms
Sleeps 11
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Mill Pond Retreat, holiday rental in Westport

Mill Pond Retreat

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Milford Beach House - New Construction!, holiday rental in Westport

Milford Beach House - New Construction!

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Elegant Country Estate with Equestrian Farm, holiday rental in Westport

Elegant Country Estate with Equestrian Farm

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

Lakeside Modern Farmhouse/Craftsman Chalet

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private 3.5 acre estate  Zen House /Historic mid century modern  / lap pool, holiday rental in Westport

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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Luxe CT Country Home w/ Hi-end WiFi for WFH & School, holiday rental in Westport

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

6 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Luxurious Retreat in the Country only 1 hour from NYC, holiday rental in Westport

Luxurious Retreat in the Country only 1 hour from NYC

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage By The Sea on Fairfield Beach, holiday rental in Westport

Charming Cottage By The Sea on Fairfield Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, holiday rental in Westport

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC, holiday rental in Westport

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

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Centrally Located Townhouse - Hotel Alternative -close to town - Pet friendly, holiday rental in Westport

Centrally Located Townhouse - Hotel Alternative -close to town - Pet friendly

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Entire Guest House at Fox Pond Farm with Access to In ground Pool, holiday rental in Westport

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

4 bedrooms
3 bathrooms
Sleeps 11
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Nice Duplex with view of Long Island Sound, holiday rental in Westport

Nice Duplex with view of Long Island Sound

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Cottage located on Historic Estate 1 Hour from NYC!, holiday rental in Westport

Charming Cottage located on Historic Estate 1 Hour from NYC!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Home for Your Family Vacation, holiday rental in Westport

Beautiful Home for Your Family Vacation

7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Elegant Beachfront, beautiful views. Come  enjoy!, holiday rental in Westport

Elegant Beachfront, beautiful views. Come enjoy!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serene Connecticut Retreat - Luxury 2 bedroom apt, holiday rental in Westport

Serene Connecticut Retreat - Luxury 2 bedroom apt

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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North Stamford Guest House, holiday rental in Westport

North Stamford Guest House

2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Brand New! Walk to Train, Downtown Fully Loaded, holiday rental in Westport

Brand New! Walk to Train, Downtown Fully Loaded

3 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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Secluded cottage on cul de sac in Rowayton., holiday rental in Westport

Secluded cottage on cul de sac in Rowayton.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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#2 - Your own place on the Beach near Silver Sands Park, holiday rental in Westport

#2 - Your own place on the Beach near Silver Sands Park

2 bedrooms
1 bathroom
Sleeps 4
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Spectacular Modern Home Near NYC, holiday rental in Westport

Spectacular Modern Home Near NYC

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Westport 'Gold Coast' across from Southport beach, holiday rental in Westport

Westport 'Gold Coast' across from Southport beach

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

Luxury Executive Estate 1 Hr from New York City

6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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#1 - A beach place by Silver Sands Park, holiday rental in Westport

#1 - A beach place by Silver Sands Park

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A New England Jewel with Scenic Beauty, holiday rental in Westport

A New England Jewel with Scenic Beauty

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Interior Designer's Enchanting And Bucolic Home, holiday rental in Westport

Interior Designer's Enchanting And Bucolic Home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Updated Farmhouse Retreat, holiday rental in Westport

Updated Farmhouse Retreat

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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A Beautiful Nature Retreat, holiday rental in Westport

A Beautiful Nature Retreat

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Greenwich Hotel Alternative / Boutique Living  - Fully Loaded- Turn Key 1B, holiday rental in Westport

Greenwich Hotel Alternative / Boutique Living - Fully Loaded- Turn Key 1B

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Nature Lovers Perfect Location, an hour from Manhattan, holiday rental in Westport

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 Westport

A Fine Waterfront Private Home, In Park-like seaing

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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See Beautiful Fall Foliage - Lovely CT country home sleeps 10 + heated  pool!, holiday rental in Westport

See Beautiful Fall Foliage - Lovely CT country home sleeps 10 + heated pool!

3 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Heart of Greenwich - Sun Drenched and Relaxing, holiday rental in Westport

Heart of Greenwich - Sun Drenched and Relaxing

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate, holiday rental in Westport

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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Large Studio by the Beach w/private entrance, holiday rental in Westport

Large Studio by the Beach w/private entrance

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fitz Haven Lovely 2-Bed Apartment in Bridgeport, holiday rental in Westport

Fitz Haven Lovely 2-Bed Apartment in Bridgeport

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy and Stylish Harbor Point Studio, holiday rental in Westport

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 Westport

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 Westport

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 Westport

Private Estate Large Private Pool

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

Lovely River view property

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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The West Lane Inn - Queen Room, holiday rental in Westport

The West Lane Inn - Queen Room

1 bedroom
1 bathroom
Sleeps 1
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