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Ashley Falls Vacation Rentals

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Bedrooms

Bathrooms

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Distance from

5 mi
47 rentals in Ashley Falls.
Luxurious Mountain Retreat - Private 40-Acre Family Haven, vacation rental in Ashley Falls
Luxurious Mountain Retreat - Private 40-Acre Family Haven, vacation rental in Ashley Falls
Luxurious Mountain Retreat - Private 40-Acre Family Haven, vacation rental in Ashley Falls

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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The following properties within 20 miles of Ashley Falls match all your filters:
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views, vacation rental in Ashley Falls
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views, vacation rental in Ashley Falls
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views, vacation rental in Ashley Falls

Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway, vacation rental in Ashley Falls
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway, vacation rental in Ashley Falls
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway, vacation rental in Ashley Falls

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Rental Home
5 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'The Mill River Cabin’ w/ Fireplace & River View!, vacation rental in Ashley Falls
'The Mill River Cabin’ w/ Fireplace & River View!, vacation rental in Ashley Falls
'The Mill River Cabin’ w/ Fireplace & River View!, vacation rental in Ashley Falls

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

Rental Home
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Ashley Falls
Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Ashley Falls
Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Ashley Falls

Gorgeous Sheffield Home in Heart of Berkshires

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, vacation rental in Ashley Falls
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, vacation rental in Ashley Falls
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, vacation rental in Ashley Falls

12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Antique Farmhouse Totally Restored, vacation rental in Ashley Falls
Antique Farmhouse Totally Restored, vacation rental in Ashley Falls
Antique Farmhouse Totally Restored, vacation rental in Ashley Falls

Antique Farmhouse Totally Restored

Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Romantic and Secluded Berkshire's Gem, vacation rental in Ashley Falls
Romantic and Secluded Berkshire's Gem, vacation rental in Ashley Falls
Romantic and Secluded Berkshire's Gem, vacation rental in Ashley Falls

Romantic and Secluded Berkshire's Gem

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Whitney by AvantStay | Private Berkshires Estate, vacation rental in Ashley Falls
Whitney by AvantStay | Private Berkshires Estate, vacation rental in Ashley Falls
Whitney by AvantStay | Private Berkshires Estate, vacation rental in Ashley Falls

Whitney by AvantStay | Private Berkshires Estate

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!, vacation rental in Ashley Falls
Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!, vacation rental in Ashley Falls
Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!, vacation rental in Ashley Falls

Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Little House in the Woods by Evergreen Home, vacation rental in Ashley Falls
Little House in the Woods by Evergreen Home, vacation rental in Ashley Falls
Little House in the Woods by Evergreen Home, vacation rental in Ashley Falls

Little House in the Woods by Evergreen Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Meadow Top Cottage: beautiful mountain views, vacation rental in Ashley Falls
Meadow Top Cottage: beautiful mountain views, vacation rental in Ashley Falls
Meadow Top Cottage: beautiful mountain views, vacation rental in Ashley Falls

Meadow Top Cottage: beautiful mountain views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Ashley Falls Getaway, vacation rental in Ashley Falls
Charming Ashley Falls Getaway, vacation rental in Ashley Falls
Charming Ashley Falls Getaway, vacation rental in Ashley Falls

Charming Ashley Falls Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Mountainside House with nearby Lake and Hiking Trails, vacation rental in Ashley Falls
Beautiful Mountainside House with nearby Lake and Hiking Trails, vacation rental in Ashley Falls
Beautiful Mountainside House with nearby Lake and Hiking Trails, vacation rental in Ashley Falls

Beautiful Mountainside House with nearby Lake and Hiking Trails

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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COME STAY AT THE SHEFFIELD CHALET!, vacation rental in Ashley Falls
COME STAY AT THE SHEFFIELD CHALET!, vacation rental in Ashley Falls
COME STAY AT THE SHEFFIELD CHALET!, vacation rental in Ashley Falls

COME STAY AT THE SHEFFIELD CHALET!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Log Cabin Retreat with Pool on 4 Acres, vacation rental in Ashley Falls
Cozy Log Cabin Retreat with Pool on 4 Acres, vacation rental in Ashley Falls
Cozy Log Cabin Retreat with Pool on 4 Acres, vacation rental in Ashley Falls

Cozy Log Cabin Retreat with Pool on 4 Acres

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!, vacation rental in Ashley Falls
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!, vacation rental in Ashley Falls
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!, vacation rental in Ashley Falls

Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, vacation rental in Ashley Falls
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, vacation rental in Ashley Falls
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, vacation rental in Ashley Falls

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Converted Berkshire schoolhouse on a quiet river, vacation rental in Ashley Falls
Converted Berkshire schoolhouse on a quiet river, vacation rental in Ashley Falls
Converted Berkshire schoolhouse on a quiet river, vacation rental in Ashley Falls

Converted Berkshire schoolhouse on a quiet river

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Skiing & Hiking: Water-View Home in the Berkshires, vacation rental in Ashley Falls
Skiing & Hiking: Water-View Home in the Berkshires, vacation rental in Ashley Falls
Skiing & Hiking: Water-View Home in the Berkshires, vacation rental in Ashley Falls

Skiing & Hiking: Water-View Home in the Berkshires

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Konkapot Cottage, Pastoral Bliss With Wide Views, vacation rental in Ashley Falls
Konkapot Cottage, Pastoral Bliss With Wide Views, vacation rental in Ashley Falls
Konkapot Cottage, Pastoral Bliss With Wide Views, vacation rental in Ashley Falls

Konkapot Cottage, Pastoral Bliss With Wide Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy Winter in the Berkshires at this cozy private getaway, vacation rental in Ashley Falls
Enjoy Winter in the Berkshires at this cozy private getaway, vacation rental in Ashley Falls
Enjoy Winter in the Berkshires at this cozy private getaway, vacation rental in Ashley Falls

Enjoy Winter in the Berkshires at this cozy private getaway

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cheerful 3-bedroom cottage with woodstove, vacation rental in Ashley Falls
Cheerful 3-bedroom cottage with woodstove, vacation rental in Ashley Falls
Cheerful 3-bedroom cottage with woodstove, vacation rental in Ashley Falls

Cheerful 3-bedroom cottage with woodstove

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Home nestled along the Blackberry River in Northwest CT, vacation rental in Ashley Falls
Spacious Home nestled along the Blackberry River in Northwest CT, vacation rental in Ashley Falls
Spacious Home nestled along the Blackberry River in Northwest CT, vacation rental in Ashley Falls

Spacious Home nestled along the Blackberry River in Northwest CT

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Fickle Fox Farm.  Leaf Peepers and Skiers! This is your season., vacation rental in Ashley Falls
Fickle Fox Farm.  Leaf Peepers and Skiers! This is your season., vacation rental in Ashley Falls
Fickle Fox Farm.  Leaf Peepers and Skiers! This is your season., vacation rental in Ashley Falls

Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful Berkshires Farmhouse with game room and plenty of room, vacation rental in Ashley Falls
Beautiful Berkshires Farmhouse with game room and plenty of room, vacation rental in Ashley Falls
Beautiful Berkshires Farmhouse with game room and plenty of room, vacation rental in Ashley Falls

Beautiful Berkshires Farmhouse with game room and plenty of room

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES, vacation rental in Ashley Falls
BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES, vacation rental in Ashley Falls
BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES, vacation rental in Ashley Falls

BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Serene Berkshire Artist's House, vacation rental in Ashley Falls
Serene Berkshire Artist's House, vacation rental in Ashley Falls
Serene Berkshire Artist's House, vacation rental in Ashley Falls

Serene Berkshire Artist's House

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BEAUTIFUL TWIN LAKES  RENTAL - Weekly or Seasonal Term Available, vacation rental in Ashley Falls
BEAUTIFUL TWIN LAKES  RENTAL - Weekly or Seasonal Term Available, vacation rental in Ashley Falls
BEAUTIFUL TWIN LAKES  RENTAL - Weekly or Seasonal Term Available, vacation rental in Ashley Falls

BEAUTIFUL TWIN LAKES RENTAL - Weekly or Seasonal Term Available

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern Farmhouse in the Southern Berkshires, vacation rental in Ashley Falls
Modern Farmhouse in the Southern Berkshires, vacation rental in Ashley Falls
Modern Farmhouse in the Southern Berkshires, vacation rental in Ashley Falls

Modern Farmhouse in the Southern Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Ashley Falls Home w/ Fire Pit: Hike & Ski!, vacation rental in Ashley Falls
Ashley Falls Home w/ Fire Pit: Hike & Ski!, vacation rental in Ashley Falls
Ashley Falls Home w/ Fire Pit: Hike & Ski!, vacation rental in Ashley Falls

Ashley Falls Home w/ Fire Pit: Hike & Ski!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly, vacation rental in Ashley Falls
Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly, vacation rental in Ashley Falls
Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly, vacation rental in Ashley Falls

Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., vacation rental in Ashley Falls
1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., vacation rental in Ashley Falls
1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., vacation rental in Ashley Falls

1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Canaan Valley Home, A Berkshires Getaway, vacation rental in Ashley Falls
Canaan Valley Home, A Berkshires Getaway, vacation rental in Ashley Falls
Canaan Valley Home, A Berkshires Getaway, vacation rental in Ashley Falls

Canaan Valley Home, A Berkshires Getaway

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!, vacation rental in Ashley Falls
Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!, vacation rental in Ashley Falls
Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!, vacation rental in Ashley Falls

Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., vacation rental in Ashley Falls
Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., vacation rental in Ashley Falls
Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., vacation rental in Ashley Falls

Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic (updated)1812 Federal brick house well situated in Berkshires with pool, vacation rental in Ashley Falls
Historic (updated)1812 Federal brick house well situated in Berkshires with pool, vacation rental in Ashley Falls
Historic (updated)1812 Federal brick house well situated in Berkshires with pool, vacation rental in Ashley Falls

Historic (updated)1812 Federal brick house well situated in Berkshires with pool

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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6 BR 'CAMP' House on Twin Lakes - Epic Historic Property, vacation rental in Ashley Falls
6 BR 'CAMP' House on Twin Lakes - Epic Historic Property, vacation rental in Ashley Falls
6 BR 'CAMP' House on Twin Lakes - Epic Historic Property, vacation rental in Ashley Falls

6 BR 'CAMP' House on Twin Lakes - Epic Historic Property

Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Berkshire Home - Enjoy summer, fall & winter attractions, vacation rental in Ashley Falls
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions, vacation rental in Ashley Falls
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions, vacation rental in Ashley Falls

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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The Blue Elm - A Historic Berkshire Cottage, vacation rental in Ashley Falls
The Blue Elm - A Historic Berkshire Cottage, vacation rental in Ashley Falls
The Blue Elm - A Historic Berkshire Cottage, vacation rental in Ashley Falls

The Blue Elm - A Historic Berkshire Cottage

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Guesthouse Cabin vacation rentals in Berkshire County, vacation rental in Ashley Falls
Guesthouse Cabin vacation rentals in Berkshire County, vacation rental in Ashley Falls
Guesthouse Cabin vacation rentals in Berkshire County, vacation rental in Ashley Falls

Guesthouse Cabin vacation rentals in Berkshire County

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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BERKSHIRE MOUNTAIN LAKEFRONT LOG HOUSE FAMILY RETREAT, vacation rental in Ashley Falls
BERKSHIRE MOUNTAIN LAKEFRONT LOG HOUSE FAMILY RETREAT, vacation rental in Ashley Falls
BERKSHIRE MOUNTAIN LAKEFRONT LOG HOUSE FAMILY RETREAT, vacation rental in Ashley Falls

BERKSHIRE MOUNTAIN LAKEFRONT LOG HOUSE FAMILY RETREAT

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Meadow Top Cottage: Countryside Cottage on 72 Acres, vacation rental in Ashley Falls
Meadow Top Cottage: Countryside Cottage on 72 Acres, vacation rental in Ashley Falls
Meadow Top Cottage: Countryside Cottage on 72 Acres, vacation rental in Ashley Falls

Meadow Top Cottage: Countryside Cottage on 72 Acres

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!, vacation rental in Ashley Falls
Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!, vacation rental in Ashley Falls
Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!, vacation rental in Ashley Falls

Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Race Mountain House, vacation rental in Ashley Falls
The Race Mountain House, vacation rental in Ashley Falls
The Race Mountain House, vacation rental in Ashley Falls

The Race Mountain House

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated, vacation rental in Ashley Falls
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated, vacation rental in Ashley Falls
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated, vacation rental in Ashley Falls

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Bellhaven- Charming 4-bedroom house in Canaan, CT, vacation rental in Ashley Falls
Bellhaven- Charming 4-bedroom house in Canaan, CT, vacation rental in Ashley Falls
Bellhaven- Charming 4-bedroom house in Canaan, CT, vacation rental in Ashley Falls

Bellhaven- Charming 4-bedroom house in Canaan, CT

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Showing results 1-47 of 47
Frequently Asked Questions about Ashley Falls