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Westhampton Holiday Rentals

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46 rentals in Westhampton.
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Waterfront Home on Pine Island Lake, holiday rental in Westhampton

Waterfront Home on Pine Island Lake

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 7, holiday rental in Westhampton

Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 7

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Big farmhouse in the foothills of the Berkshires, holiday rental in Westhampton

Big farmhouse in the foothills of the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hadley/Amherst Awesome Location.Exploration of Everything in the Pioneer Valley!, holiday rental in Westhampton

Hadley/Amherst Awesome Location.Exploration of Everything in the Pioneer Valley!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL, holiday rental in Westhampton

COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A-Frame in Sherwood Forest, holiday rental in Westhampton

A-Frame in Sherwood Forest

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Elegant Wilderness Cabin 12 Miles From Northampton, holiday rental in Westhampton

Elegant Wilderness Cabin 12 Miles From Northampton

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious waterfront Berkshire home family private get-away, holiday rental in Westhampton

Spacious waterfront Berkshire home family private get-away

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Remote and Relaxing Cabin in the Berkshires, holiday rental in Westhampton

Remote and Relaxing Cabin in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful four season lakeside log home close to all Berkshires attractions., holiday rental in Westhampton

Beautiful four season lakeside log home close to all Berkshires attractions.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Serene & cozy lakefront getaway on Congamond's pristine North Pond, holiday rental in Westhampton

Serene & cozy lakefront getaway on Congamond's pristine North Pond

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, holiday rental in Westhampton

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Peace And Quiet On The Lake, holiday rental in Westhampton

Peace And Quiet On The Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront home with direct lake access, private sandy beach, holiday rental in Westhampton

Beachfront home with direct lake access, private sandy beach

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cottage In The Berkshires In Western Massachusetts, holiday rental in Westhampton

Lakefront Cottage In The Berkshires In Western Massachusetts

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fully renovated lakeview Cottage, Southwick,  MA, holiday rental in Westhampton

Fully renovated lakeview Cottage, Southwick, MA

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming cedar shingle cottage, holiday rental in Westhampton

Charming cedar shingle cottage

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Scenic ByWay Waterfront Property, holiday rental in Westhampton

Scenic ByWay Waterfront Property

3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style, holiday rental in Westhampton

Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Bershire Home Rental:  Enjoy Berkshire Fall Foliage, holiday rental in Westhampton

Bershire Home Rental: Enjoy Berkshire Fall Foliage

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Ashmere Lake Log Cabin with privacy / 2 Bedrooms, holiday rental in Westhampton

Ashmere Lake Log Cabin with privacy / 2 Bedrooms

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sunset Place - Modern Lake House on Otis Reservoir - 5 Night Min Stay - Sleeps 6, holiday rental in Westhampton

Sunset Place - Modern Lake House on Otis Reservoir - 5 Night Min Stay - Sleeps 6

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Westhampton

Berkshire house w/ fireplace, A/C, WiFi & laundry

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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5BD Downtown Brownstone - 3 blocks from MGM Casino, holiday rental in Westhampton

5BD Downtown Brownstone - 3 blocks from MGM Casino

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Flight's End-A Country Home with Babbling Brook, holiday rental in Westhampton

Flight's End-A Country Home with Babbling Brook

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View, holiday rental in Westhampton

A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Escape to the Berkshires!, holiday rental in Westhampton

Escape to the Berkshires!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quiet Comfortable Cabin 5 Min. Walk to Lake, holiday rental in Westhampton

Quiet Comfortable Cabin 5 Min. Walk to Lake

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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4 Bedroom House Close to UMass/Amherst, Historic Deerfield & Yankee Candle, holiday rental in Westhampton

4 Bedroom House Close to UMass/Amherst, Historic Deerfield & Yankee Candle

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lily's Lodge, holiday rental in Westhampton

Lily's Lodge

2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Enjoy horses and the largest recreational lake in Massachusetts, holiday rental in Westhampton

Enjoy horses and the largest recreational lake in Massachusetts

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Corner Cottage in 16 Acres Springfield, holiday rental in Westhampton

Corner Cottage in 16 Acres Springfield

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall,, holiday rental in Westhampton

Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall,

7 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Beautiful Berkshire Home in Private Community, holiday rental in Westhampton

Beautiful Berkshire Home in Private Community

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, holiday rental in Westhampton

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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OWL'S NEST LODGING, holiday rental in Westhampton

OWL'S NEST LODGING

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES, holiday rental in Westhampton

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Starlight Llama - The White Room, holiday rental in Westhampton

Starlight Llama - The White Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Starlight Llama - The Pink Room, holiday rental in Westhampton

Starlight Llama - The Pink Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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UPSCALEDHOME IN A QUIET NEIGHBORHOOD. ENTIRE4BED HOME TO YOURSELF Co-Vid 19 Safe, holiday rental in Westhampton

UPSCALEDHOME IN A QUIET NEIGHBORHOOD. ENTIRE4BED HOME TO YOURSELF Co-Vid 19 Safe

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Maple Corner Farm's Meadow Site, holiday rental in Westhampton

Tentrr Signature Site - Maple Corner Farm's Meadow Site

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Tamarack at Running Fox Berry Farm, holiday rental in Westhampton

Tentrr Signature Site - Tamarack at Running Fox Berry Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Rural Berkshires Home, holiday rental in Westhampton

Rural Berkshires Home

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fair Vacation rentals, holiday rental in Westhampton

Fair Vacation rentals

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lake house in the heart of the Berkshires, holiday rental in Westhampton

Lake house in the heart of the Berkshires

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Springfield rental- close to MGM And Basket ball hall of fame, holiday rental in Westhampton

Beautiful Springfield rental- close to MGM And Basket ball hall of fame

5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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