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Ashfield Holiday Rentals

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41 rentals in Ashfield.
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A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View, holiday rental in Ashfield

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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Rural Berkshires Home, holiday rental in Ashfield

Rural Berkshires Home

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Unique People & Pet-Welcoming Country Haven, holiday rental in Ashfield

Unique People & Pet-Welcoming Country Haven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, holiday rental in Ashfield

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont!  Come Explore!, holiday rental in Ashfield

Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont! Come Explore!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home on Pine Island Lake, holiday rental in Ashfield

Waterfront Home on Pine Island Lake

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

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 Ashfield

Elegant Wilderness Cabin 12 Miles From Northampton

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Rustic House Overlooking The Deerfield River, holiday rental in Ashfield

Modern Rustic House Overlooking The Deerfield River

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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In town, newly remodeled studio with private balcony, holiday rental in Ashfield

In town, newly remodeled studio with private balcony

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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19th c. Renovated Barn in the Berkshires, holiday rental in Ashfield

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming New England House Surrounded By Trees, Field And Pond, holiday rental in Ashfield

Charming New England House Surrounded By Trees, Field And Pond

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Remote and Relaxing Cabin in the Berkshires, holiday rental in Ashfield

Remote and Relaxing Cabin in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sweet Spot in a Region that Shines in Every Season, holiday rental in Ashfield

Sweet Spot in a Region that Shines in Every Season

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, holiday rental in Ashfield

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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1810 Brook Side Mill/House / Winter Fun Getaway in Western MA, holiday rental in Ashfield

1810 Brook Side Mill/House / Winter Fun Getaway in Western MA

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous modern Country Home, holiday rental in Ashfield

Gorgeous modern Country Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Rural Cottage in the Heart of the Scenic Mohawk Trail, holiday rental in Ashfield

Charming Rural Cottage in the Heart of the Scenic Mohawk Trail

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Charming Affordable  Home for groups up to 14, holiday rental in Ashfield

Charming Affordable Home for groups up to 14

7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Retreat in the Woods, holiday rental in Ashfield

Retreat in the Woods

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spring Escape, Get away in the falls❤️, holiday rental in Ashfield

Spring Escape, Get away in the falls❤️

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Vermont Log Cabin available for weekend and weekly, holiday rental in Ashfield

Vermont Log Cabin available for weekend and weekly

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Ashfield

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

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

Flight's End-A Country Home with Babbling Brook

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bright three-level home w/water views, jetted tub, firepit, and more!, holiday rental in Ashfield

Bright three-level home w/water views, jetted tub, firepit, and more!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun, holiday rental in Ashfield

Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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4 Bedroom House Close to UMass/Amherst, Historic Deerfield & Yankee Candle, holiday rental in Ashfield

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

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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PARADISE on EARTH! - Historic 4BR Farmhouse, holiday rental in Ashfield

PARADISE on EARTH! - Historic 4BR Farmhouse

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, holiday rental in Ashfield

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 Ashfield

OWL'S NEST LODGING

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Starlight Llama - The Lavender Room, holiday rental in Ashfield

Starlight Llama - The Lavender Room

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

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 Ashfield

Starlight Llama - The Pink Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Serene Shelburne Studio Cabin w/Spring-Fed Pool!, holiday rental in Ashfield

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tibet House, holiday rental in Ashfield

Tibet House

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Bear Den, holiday rental in Ashfield

The Bear Den

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Picturesque Cottage with Sunroom on Ashmere Lake!, holiday rental in Ashfield

Picturesque Cottage with Sunroom on Ashmere Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Hidden Hoosic   Riverside Camp, holiday rental in Ashfield

Tentrr Signature Site - Hidden Hoosic Riverside Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Tamarack at Running Fox Berry Farm, holiday rental in Ashfield

Tentrr Signature Site - Tamarack at Running Fox Berry Farm

1 bedroom
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 Ashfield

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

7 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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NEW! Kid-Friendly & Views! Hike, Bike, Grill, Swim, holiday rental in Ashfield

NEW! Kid-Friendly & Views! Hike, Bike, Grill, Swim

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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