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Hampshire County Holiday Rentals

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44 rentals in Hampshire County.
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Waterfront Home on Pine Island Lake, holiday rental in Hampshire County
Waterfront Home on Pine Island Lake, holiday rental in Hampshire County
Waterfront Home on Pine Island Lake, holiday rental in Hampshire County

Waterfront Home on Pine Island Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Be Home In Heart Of Northampton's Smith College Neighborhood, holiday rental in Hampshire County
Be Home In Heart Of Northampton's Smith College Neighborhood, holiday rental in Hampshire County
Be Home In Heart Of Northampton's Smith College Neighborhood, holiday rental in Hampshire County

Be Home In Heart Of Northampton's Smith College Neighborhood

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountain View: Comfort and Calm., holiday rental in Hampshire County
Mountain View: Comfort and Calm., holiday rental in Hampshire County
Mountain View: Comfort and Calm., holiday rental in Hampshire County

Mountain View: Comfort and Calm.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Elegant Wilderness Cabin 12 Miles From Northampton, holiday rental in Hampshire County
Elegant Wilderness Cabin 12 Miles From Northampton, holiday rental in Hampshire County
Elegant Wilderness Cabin 12 Miles From Northampton, holiday rental in Hampshire County

Elegant Wilderness Cabin 12 Miles From Northampton

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Northampton Area Home on 8 Lush Acres, holiday rental in Hampshire County
Private Northampton Area Home on 8 Lush Acres, holiday rental in Hampshire County
Private Northampton Area Home on 8 Lush Acres, holiday rental in Hampshire County

Private Northampton Area Home on 8 Lush Acres

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, holiday rental in Hampshire County
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, holiday rental in Hampshire County
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, holiday rental in Hampshire County

Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens, holiday rental in Hampshire County
Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens, holiday rental in Hampshire County
Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens, holiday rental in Hampshire County

Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bamboo:  Spacious with Cedar Wet-room., holiday rental in Hampshire County
Bamboo:  Spacious with Cedar Wet-room., holiday rental in Hampshire County
Bamboo:  Spacious with Cedar Wet-room., holiday rental in Hampshire County

Bamboo: Spacious with Cedar Wet-room.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hadley/Amherst Awesome Location.Exploration of Everything in the Pioneer Valley!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Private Elegant 2 Bedroom Close To Everything In The Valley, holiday rental in Hampshire County
Private Elegant 2 Bedroom Close To Everything In The Valley, holiday rental in Hampshire County
Private Elegant 2 Bedroom Close To Everything In The Valley, holiday rental in Hampshire County

Private Elegant 2 Bedroom Close To Everything In The Valley

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, holiday rental in Hampshire County
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, holiday rental in Hampshire County
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, holiday rental in Hampshire County

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Creation Station is a cozy place so make yourself at home., holiday rental in Hampshire County
The Creation Station is a cozy place so make yourself at home., holiday rental in Hampshire County
The Creation Station is a cozy place so make yourself at home., holiday rental in Hampshire County

The Creation Station is a cozy place so make yourself at home.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Hampshire County
Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Hampshire County
Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Hampshire County

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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comfort, luxury, privacy, holiday rental in Hampshire County
comfort, luxury, privacy, holiday rental in Hampshire County
comfort, luxury, privacy, holiday rental in Hampshire County

comfort, luxury, privacy

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!, holiday rental in Hampshire County
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!, holiday rental in Hampshire County
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!, holiday rental in Hampshire County

Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, holiday rental in Hampshire County
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, holiday rental in Hampshire County
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, holiday rental in Hampshire County

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, holiday rental in Hampshire County
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, holiday rental in Hampshire County
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, holiday rental in Hampshire County

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Farmhouse - quiet, private & peaceful, holiday rental in Hampshire County
Charming Farmhouse - quiet, private & peaceful, holiday rental in Hampshire County
Charming Farmhouse - quiet, private & peaceful, holiday rental in Hampshire County

Charming Farmhouse - quiet, private & peaceful

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 8, holiday rental in Hampshire County
Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 8, holiday rental in Hampshire County
Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 8, holiday rental in Hampshire County

Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 8

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Designer Guest Suite on Historic New England Homestead, holiday rental in Hampshire County
Designer Guest Suite on Historic New England Homestead, holiday rental in Hampshire County
Designer Guest Suite on Historic New England Homestead, holiday rental in Hampshire County

Designer Guest Suite on Historic New England Homestead

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cheerful 1 bedroom, holiday rental in Hampshire County
Cheerful 1 bedroom, holiday rental in Hampshire County
Cheerful 1 bedroom, holiday rental in Hampshire County

Cheerful 1 bedroom

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming, newly renovated, 3 bedroom farmhouse, holiday rental in Hampshire County
Charming, newly renovated, 3 bedroom farmhouse, holiday rental in Hampshire County
Charming, newly renovated, 3 bedroom farmhouse, holiday rental in Hampshire County

Charming, newly renovated, 3 bedroom farmhouse

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Fenced in back yard, gardens, barn view and easy access to area attractions, holiday rental in Hampshire County
Fenced in back yard, gardens, barn view and easy access to area attractions, holiday rental in Hampshire County
Fenced in back yard, gardens, barn view and easy access to area attractions, holiday rental in Hampshire County

Fenced in back yard, gardens, barn view and easy access to area attractions

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Cozy apartment located in quiet Williamsburg, holiday rental in Hampshire County
Cozy apartment located in quiet Williamsburg, holiday rental in Hampshire County
Cozy apartment located in quiet Williamsburg, holiday rental in Hampshire County

Cozy apartment located in quiet Williamsburg

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall,, holiday rental in Hampshire County
Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall,, holiday rental in Hampshire County
Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall,, holiday rental in Hampshire County

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

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Starlight Llama - The White Room, holiday rental in Hampshire County
Starlight Llama - The White Room, holiday rental in Hampshire County
Starlight Llama - The White Room, holiday rental in Hampshire County

Starlight Llama - The White Room

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cute two bedroom , holiday rental in Hampshire County
Cute two bedroom , holiday rental in Hampshire County
Cute two bedroom , holiday rental in Hampshire County

Cute two bedroom

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront Summer Cottage~Sparkling clean social distancing space, holiday rental in Hampshire County
Lakefront Summer Cottage~Sparkling clean social distancing space, holiday rental in Hampshire County
Lakefront Summer Cottage~Sparkling clean social distancing space, holiday rental in Hampshire County

Lakefront Summer Cottage~Sparkling clean social distancing space

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront Summer Cottages~Sparkling clean social distancing space!, holiday rental in Hampshire County
Lakefront Summer Cottages~Sparkling clean social distancing space!, holiday rental in Hampshire County
Lakefront Summer Cottages~Sparkling clean social distancing space!, holiday rental in Hampshire County

Lakefront Summer Cottages~Sparkling clean social distancing space!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Starlight Llama - The Pink Room, holiday rental in Hampshire County
Starlight Llama - The Pink Room, holiday rental in Hampshire County
Starlight Llama - The Pink Room, holiday rental in Hampshire County

Starlight Llama - The Pink Room

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Detached, Spotless 3 Bd. Home - Sleeps 7, holiday rental in Hampshire County
Detached, Spotless 3 Bd. Home - Sleeps 7, holiday rental in Hampshire County
Detached, Spotless 3 Bd. Home - Sleeps 7, holiday rental in Hampshire County

Detached, Spotless 3 Bd. Home - Sleeps 7

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Tamarack at Running Fox Berry Farm, holiday rental in Hampshire County
Tentrr Signature Site - Tamarack at Running Fox Berry Farm, holiday rental in Hampshire County
Tentrr Signature Site - Tamarack at Running Fox Berry Farm, holiday rental in Hampshire County

Tentrr Signature Site - Tamarack at Running Fox Berry Farm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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A cozy rest in  tiny home of a nest (downtown Northampton), holiday rental in Hampshire County
A cozy rest in  tiny home of a nest (downtown Northampton), holiday rental in Hampshire County
A cozy rest in  tiny home of a nest (downtown Northampton), holiday rental in Hampshire County

A cozy rest in tiny home of a nest (downtown Northampton)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Mountain View! Spacious, private in law suite, holiday rental in Hampshire County
Mountain View! Spacious, private in law suite, holiday rental in Hampshire County
Mountain View! Spacious, private in law suite, holiday rental in Hampshire County

Mountain View! Spacious, private in law suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Rest in the Noho Nest, holiday rental in Hampshire County
Rest in the Noho Nest, holiday rental in Hampshire County
Rest in the Noho Nest, holiday rental in Hampshire County

Rest in the Noho Nest

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Low scent, charming, quiet house with large yard., holiday rental in Hampshire County
Low scent, charming, quiet house with large yard., holiday rental in Hampshire County
Low scent, charming, quiet house with large yard., holiday rental in Hampshire County

Low scent, charming, quiet house with large yard.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Furnished Rental monthly/weekly rental with discount!, holiday rental in Hampshire County
Furnished Rental monthly/weekly rental with discount!, holiday rental in Hampshire County
Furnished Rental monthly/weekly rental with discount!, holiday rental in Hampshire County

Furnished Rental monthly/weekly rental with discount!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Birch Suite- 2nd Floor Apartment with Kitchenette, holiday rental in Hampshire County
Birch Suite- 2nd Floor Apartment with Kitchenette, holiday rental in Hampshire County
Birch Suite- 2nd Floor Apartment with Kitchenette, holiday rental in Hampshire County

Birch Suite- 2nd Floor Apartment with Kitchenette

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Low-scent, Northampton historic mill house, holiday rental in Hampshire County
Low-scent, Northampton historic mill house, holiday rental in Hampshire County
Low-scent, Northampton historic mill house, holiday rental in Hampshire County

Low-scent, Northampton historic mill house

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Maple Suite- Private Ground Floor Apartment, holiday rental in Hampshire County
Maple Suite- Private Ground Floor Apartment, holiday rental in Hampshire County
Maple Suite- Private Ground Floor Apartment, holiday rental in Hampshire County

Maple Suite- Private Ground Floor Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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NEW! Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!, holiday rental in Hampshire County
NEW! Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!, holiday rental in Hampshire County
NEW! Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!, holiday rental in Hampshire County

NEW! Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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A simple kind of paradise, holiday rental in Hampshire County
A simple kind of paradise, holiday rental in Hampshire County
A simple kind of paradise, holiday rental in Hampshire County

A simple kind of paradise

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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River Run - renovated farmhouse with tennis court, holiday rental in Hampshire County
River Run - renovated farmhouse with tennis court, holiday rental in Hampshire County
River Run - renovated farmhouse with tennis court, holiday rental in Hampshire County

River Run - renovated farmhouse with tennis court

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Huntington Home - Walk to Westfield River, holiday rental in Hampshire County
Historic Huntington Home - Walk to Westfield River, holiday rental in Hampshire County
Historic Huntington Home - Walk to Westfield River, holiday rental in Hampshire County

Historic Huntington Home - Walk to Westfield River

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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