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New Ashford Vacation Rentals

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Bedrooms

Bathrooms

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Distance from

5 mi
45 rentals in New Ashford.
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in New Ashford
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in New Ashford
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in New Ashford

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Huge Beautiful House-2 families-16 Acres -Low rates- 2 min from Jiminy Peak, vacation rental in New Ashford
Huge Beautiful House-2 families-16 Acres -Low rates- 2 min from Jiminy Peak, vacation rental in New Ashford
Huge Beautiful House-2 families-16 Acres -Low rates- 2 min from Jiminy Peak, vacation rental in New Ashford

Huge Beautiful House-2 families-16 Acres -Low rates- 2 min from Jiminy Peak

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Elegant Mountain View Retreat By Evergreen Home, vacation rental in New Ashford
Elegant Mountain View Retreat By Evergreen Home, vacation rental in New Ashford
Elegant Mountain View Retreat By Evergreen Home, vacation rental in New Ashford

Elegant Mountain View Retreat By Evergreen Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The following properties within 20 miles of New Ashford match all your filters:
Bentley Brook at Jiminy Peak ^ Studio, vacation rental in New Ashford
Bentley Brook at Jiminy Peak ^ Studio, vacation rental in New Ashford
Bentley Brook at Jiminy Peak ^ Studio, vacation rental in New Ashford

Bentley Brook at Jiminy Peak ^ Studio

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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ONTARA...., vacation rental in New Ashford
ONTARA...., vacation rental in New Ashford
ONTARA...., vacation rental in New Ashford

ONTARA....

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Embrace the Berkshires, vacation rental in New Ashford
Embrace the Berkshires, vacation rental in New Ashford
Embrace the Berkshires, vacation rental in New Ashford

Embrace the Berkshires

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming A-Frame Near all the Best parts of the Berkshires!, vacation rental in New Ashford
Charming A-Frame Near all the Best parts of the Berkshires!, vacation rental in New Ashford
Charming A-Frame Near all the Best parts of the Berkshires!, vacation rental in New Ashford

Charming A-Frame Near all the Best parts of the Berkshires!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps
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Family-friendly, private three bedroom cottage in the beautiful Berkshires, vacation rental in New Ashford
Family-friendly, private three bedroom cottage in the beautiful Berkshires, vacation rental in New Ashford
Family-friendly, private three bedroom cottage in the beautiful Berkshires, vacation rental in New Ashford

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Berkshire Cabin on 27acres near Jiminy Peak., vacation rental in New Ashford
Private Berkshire Cabin on 27acres near Jiminy Peak., vacation rental in New Ashford
Private Berkshire Cabin on 27acres near Jiminy Peak., vacation rental in New Ashford

Private Berkshire Cabin on 27acres near Jiminy Peak.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in New Ashford
Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in New Ashford
Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in New Ashford

Jiminy Peak Mountainside Getaway in the Berkshires

Rental Home
3 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Large, family-friendly farmhouse located in the beautiful Berkshires, vacation rental in New Ashford
Large, family-friendly farmhouse located in the beautiful Berkshires, vacation rental in New Ashford
Large, family-friendly farmhouse located in the beautiful Berkshires, vacation rental in New Ashford

Large, family-friendly farmhouse located in the beautiful Berkshires

Rental Home
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly., vacation rental in New Ashford
Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly., vacation rental in New Ashford
Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly., vacation rental in New Ashford

Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet, vacation rental in New Ashford
Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet, vacation rental in New Ashford
Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet, vacation rental in New Ashford

Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Escape to Serenity: Unplug in the Berkshires!, vacation rental in New Ashford
Escape to Serenity: Unplug in the Berkshires!, vacation rental in New Ashford
Escape to Serenity: Unplug in the Berkshires!, vacation rental in New Ashford

Escape to Serenity: Unplug in the Berkshires!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, vacation rental in New Ashford
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, vacation rental in New Ashford
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, vacation rental in New Ashford

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!, vacation rental in New Ashford
2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!, vacation rental in New Ashford
2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!, vacation rental in New Ashford

2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak, vacation rental in New Ashford
Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak, vacation rental in New Ashford
Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak, vacation rental in New Ashford

Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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2br DX Condo Ski & Berkshire County!, vacation rental in New Ashford
2br DX Condo Ski & Berkshire County!, vacation rental in New Ashford
2br DX Condo Ski & Berkshire County!, vacation rental in New Ashford

2br DX Condo Ski & Berkshire County!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mountainside: Large 3-level Jiminy Peak Home, vacation rental in New Ashford
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in New Ashford
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in New Ashford

Mountainside: Large 3-level Jiminy Peak Home

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, vacation rental in New Ashford
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, vacation rental in New Ashford
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, vacation rental in New Ashford

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in New Ashford
Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in New Ashford
Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in New Ashford

Wyndham Bentley Brook Jiminy Peak ski in/out unit

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Studio Suite, w/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!, vacation rental in New Ashford
Studio Suite, w/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!, vacation rental in New Ashford
Studio Suite, w/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!, vacation rental in New Ashford

Studio Suite, w/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Pres Week- Bentley Brook Resort - Your Peak Winter Escape, vacation rental in New Ashford
Pres Week- Bentley Brook Resort - Your Peak Winter Escape, vacation rental in New Ashford
Pres Week- Bentley Brook Resort - Your Peak Winter Escape, vacation rental in New Ashford

Pres Week- Bentley Brook Resort - Your Peak Winter Escape

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable Berkshires retreat on mtn resort, SISO, vacation rental in New Ashford
Comfortable Berkshires retreat on mtn resort, SISO, vacation rental in New Ashford
Comfortable Berkshires retreat on mtn resort, SISO, vacation rental in New Ashford

Comfortable Berkshires retreat on mtn resort, SISO

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Home in the Berkshires, vacation rental in New Ashford
Home in the Berkshires, vacation rental in New Ashford
Home in the Berkshires, vacation rental in New Ashford

Home in the Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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2 Bedroom Deluxe Condo at Jiminy Peak Ski Mountain, Bentley Brook Resort!, vacation rental in New Ashford
2 Bedroom Deluxe Condo at Jiminy Peak Ski Mountain, Bentley Brook Resort!, vacation rental in New Ashford
2 Bedroom Deluxe Condo at Jiminy Peak Ski Mountain, Bentley Brook Resort!, vacation rental in New Ashford

2 Bedroom Deluxe Condo at Jiminy Peak Ski Mountain, Bentley Brook Resort!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in New Ashford

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in New Ashford
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in New Ashford
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in New Ashford

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Wyndham Bentley Brook ~ Winter Recess, vacation rental in New Ashford
Wyndham Bentley Brook ~ Winter Recess, vacation rental in New Ashford
Wyndham Bentley Brook ~ Winter Recess, vacation rental in New Ashford

Wyndham Bentley Brook ~ Winter Recess

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in New Ashford
Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in New Ashford
Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in New Ashford

Bentley Brook ski in/ski out at Jiminy Peak

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Ski resort, vacation rental in New Ashford
Ski resort, vacation rental in New Ashford
Ski resort, vacation rental in New Ashford

Ski resort

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
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2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!, vacation rental in New Ashford
2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!, vacation rental in New Ashford
2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!, vacation rental in New Ashford

2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Vacation Village In The Berkshires 5 Star Resort - Suite B, vacation rental in New Ashford
Vacation Village In The Berkshires 5 Star Resort - Suite B, vacation rental in New Ashford
Vacation Village In The Berkshires 5 Star Resort - Suite B, vacation rental in New Ashford

Vacation Village In The Berkshires 5 Star Resort - Suite B

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Berkshires Living!! Beautiful Location, Breathtaking Sunsets, Fully Reno Home, vacation rental in New Ashford
Berkshires Living!! Beautiful Location, Breathtaking Sunsets, Fully Reno Home, vacation rental in New Ashford
Berkshires Living!! Beautiful Location, Breathtaking Sunsets, Fully Reno Home, vacation rental in New Ashford

Berkshires Living!! Beautiful Location, Breathtaking Sunsets, Fully Reno Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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1 Bedroom - Vacation Village in the Berkshires Resort - Hancock, vacation rental in New Ashford
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock, vacation rental in New Ashford
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock, vacation rental in New Ashford

1 Bedroom - Vacation Village in the Berkshires Resort - Hancock

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely Home for Your Berkshires Trip, Clark Museum or MASS MoCA Visit, vacation rental in New Ashford
Lovely Home for Your Berkshires Trip, Clark Museum or MASS MoCA Visit, vacation rental in New Ashford
Lovely Home for Your Berkshires Trip, Clark Museum or MASS MoCA Visit, vacation rental in New Ashford

Lovely Home for Your Berkshires Trip, Clark Museum or MASS MoCA Visit

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!, vacation rental in New Ashford
2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!, vacation rental in New Ashford
2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!, vacation rental in New Ashford

2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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2 Bedroom Deluxe Condo w/ Kitchen at Bentley Brook, Jiminy Peak Ski Mountain!!, vacation rental in New Ashford
2 Bedroom Deluxe Condo w/ Kitchen at Bentley Brook, Jiminy Peak Ski Mountain!!, vacation rental in New Ashford
2 Bedroom Deluxe Condo w/ Kitchen at Bentley Brook, Jiminy Peak Ski Mountain!!, vacation rental in New Ashford

2 Bedroom Deluxe Condo w/ Kitchen at Bentley Brook, Jiminy Peak Ski Mountain!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Bentley Brook at Jiminy Peak ^^ 2 Bedroom, vacation rental in New Ashford
Bentley Brook at Jiminy Peak ^^ 2 Bedroom, vacation rental in New Ashford
Bentley Brook at Jiminy Peak ^^ 2 Bedroom, vacation rental in New Ashford

Bentley Brook at Jiminy Peak ^^ 2 Bedroom

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook Condo Resort, vacation rental in New Ashford
Wyndham Bentley Brook Condo Resort, vacation rental in New Ashford
Wyndham Bentley Brook Condo Resort, vacation rental in New Ashford

Wyndham Bentley Brook Condo Resort

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook 2 Bedroom Deluxe, In & Out Ski Resort at Jiminy Peak, vacation rental in New Ashford
Wyndham Bentley Brook 2 Bedroom Deluxe, In & Out Ski Resort at Jiminy Peak, vacation rental in New Ashford
Wyndham Bentley Brook 2 Bedroom Deluxe, In & Out Ski Resort at Jiminy Peak, vacation rental in New Ashford

Wyndham Bentley Brook 2 Bedroom Deluxe, In & Out Ski Resort at Jiminy Peak

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort, vacation rental in New Ashford
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort, vacation rental in New Ashford
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort, vacation rental in New Ashford

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Rental Home
1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA, vacation rental in New Ashford
Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA, vacation rental in New Ashford
Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA, vacation rental in New Ashford

Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-45 of 45
Frequently Asked Questions about New Ashford