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Ashley Falls Holiday Rentals

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50 rentals in Ashley Falls.
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Charming Ashley Falls Cottage Retreat, holiday rental in Ashley Falls

Charming Ashley Falls Cottage Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ski Retreat -- Private Modern on 40 Acres of Land, holiday rental in Ashley Falls

Ski Retreat -- Private Modern on 40 Acres of Land

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Close To Skiing!  Beautiful +Family Friendly - W Tree House & Tennis Court, holiday rental in Ashley Falls

Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Room to Roam. Modern home with all amenities + sep. cabin on 10+  wooded acres., holiday rental in Ashley Falls

Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Antique Farmhouse Totally Restored, holiday rental in Ashley Falls

Antique Farmhouse Totally Restored

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Private rustic cottage with lake access, holiday rental in Ashley Falls

Private rustic cottage with lake access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Log Cabin in the Berkshires, holiday rental in Ashley Falls

Gorgeous Log Cabin in the Berkshires

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Downtown GB apartment walk to shops and restaurants, holiday rental in Ashley Falls

Downtown GB apartment walk to shops and restaurants

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Stunning Renovated Victorian, holiday rental in Ashley Falls

Stunning Renovated Victorian

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., holiday rental in Ashley Falls

Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Southfield Village!, holiday rental in Ashley Falls

Beautiful Southfield Village!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Harmony House, Lakeville, Connecticut, holiday rental in Ashley Falls

Harmony House, Lakeville, Connecticut

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Spacious Country Retreat With Secluded Tree Top Mountain Views, holiday rental in Ashley Falls

Spacious Country Retreat With Secluded Tree Top Mountain Views

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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North Canaan's Quiet & Cozy Home, holiday rental in Ashley Falls

North Canaan's Quiet & Cozy Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Little House in the Woods, holiday rental in Ashley Falls

The Little House in the Woods

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake Community - Near Town, Attractions, holiday rental in Ashley Falls

Lake Community - Near Town, Attractions

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Cottage at Great Falls, holiday rental in Ashley Falls

The Cottage at Great Falls

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Barn - Rustic Chic Loft - Rehabed 1890 Hay Barn - Near Lakes & Hotchkiss, holiday rental in Ashley Falls

The Barn - Rustic Chic Loft - Rehabed 1890 Hay Barn - Near Lakes & Hotchkiss

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Mountainside House with nearby Lake and Hiking Trails, holiday rental in Ashley Falls

Beautiful Mountainside House with nearby Lake and Hiking Trails

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions, holiday rental in Ashley Falls

Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW SECLUDED 3 BEDROOM COUNTRY CASTLE, holiday rental in Ashley Falls

NEW SECLUDED 3 BEDROOM COUNTRY CASTLE

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington., holiday rental in Ashley Falls

Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, holiday rental in Ashley Falls

PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington, holiday rental in Ashley Falls

Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Country Retreat-Berkshires, holiday rental in Ashley Falls

Newly Renovated Country Retreat-Berkshires

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Converted Berkshire schoolhouse on a quiet river, holiday rental in Ashley Falls

Converted Berkshire schoolhouse on a quiet river

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut, holiday rental in Ashley Falls

Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Gem of the Berkshires, walk to downtown & lake., holiday rental in Ashley Falls

Gem of the Berkshires, walk to downtown & lake.

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn, holiday rental in Ashley Falls

Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Victorian on the Hill, holiday rental in Ashley Falls

Modern Victorian on the Hill

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Konkapot Cottage, Pastoral Bliss With Wide Views, holiday rental in Ashley Falls

Konkapot Cottage, Pastoral Bliss With Wide Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Farmhouse in the Southern Berkshires, holiday rental in Ashley Falls

Modern Farmhouse in the Southern Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing, holiday rental in Ashley Falls

Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing

0 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming 2+2 Lakeside Cottage on Best Lake in CT, holiday rental in Ashley Falls

Charming 2+2 Lakeside Cottage on Best Lake in CT

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lake House, holiday rental in Ashley Falls

Lake House

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, holiday rental in Ashley Falls

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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'The Mill River Cabin’ w/ Fireplace & River View!, holiday rental in Ashley Falls

'The Mill River Cabin’ w/ Fireplace & River View!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Fabulous Post & Beam Berkshire Rental, holiday rental in Ashley Falls

Fabulous Post & Beam Berkshire Rental

0 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Renovated Lakefront House w/ Dock: Pets Welcome!, holiday rental in Ashley Falls

Renovated Lakefront House w/ Dock: Pets Welcome!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Private Home Overlooking Stevens Lake, holiday rental in Ashley Falls

Private Home Overlooking Stevens Lake

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Echo Hill, holiday rental in Ashley Falls

Tentrr Signature Site - Echo Hill

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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NEW! Cozy Great Barrington Home 1 Mi to Ski Resort, holiday rental in Ashley Falls

NEW! Cozy Great Barrington Home 1 Mi to Ski Resort

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site C, holiday rental in Ashley Falls

Tentrr State Park Site - Taconic State Park: High Valley Rd Site C

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site B, holiday rental in Ashley Falls

Tentrr State Park Site - Taconic State Park: High Valley Rd Site B

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site A, holiday rental in Ashley Falls

Tentrr State Park Site - Taconic State Park: High Valley Rd Site A

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site D, holiday rental in Ashley Falls

Tentrr State Park Site - Taconic State Park: High Valley Rd Site D

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular Fall Foliage in Sheffield  with Monthly Special Pricing Available, holiday rental in Ashley Falls

Spectacular Fall Foliage in Sheffield with Monthly Special Pricing Available

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!, holiday rental in Ashley Falls

Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Central Berkshires Cottage: Hot Tub, Fire Pit, holiday rental in Ashley Falls

NEW! Central Berkshires Cottage: Hot Tub, Fire Pit

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Berkshire Getaway Walk to Winery brewery and distillery!, holiday rental in Ashley Falls

Cozy Berkshire Getaway Walk to Winery brewery and distillery!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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