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Holiday Homes in Canaan

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50 rentals in Canaan.
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Cedar Chest, holiday rental in Canaan

Cedar Chest

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beauty in the Berkshires, holiday rental in Canaan

Beauty in the Berkshires

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Recently renovated 4 bedroom lakefront house in The Berkshires., holiday rental in Canaan

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Berkshire Farmhouse Vacation, holiday rental in Canaan

Berkshire Farmhouse Vacation

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., holiday rental in Canaan

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vacation in a  Berkshire Farmhouse, holiday rental in Canaan

Vacation in a Berkshire Farmhouse

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Tranquil Lake House Getaway on Onota Lake, holiday rental in Canaan

Tranquil Lake House Getaway on Onota Lake

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., holiday rental in Canaan

4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, holiday rental in Canaan

Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., holiday rental in Canaan

Warm your heart this holiday season in this cozy cottage next to downtown Lenox.

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Farmhouse Steps from Downtown West Stockbridge, holiday rental in Canaan

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE, holiday rental in Canaan

CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b, holiday rental in Canaan

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful 3 BR Berkshire Home - Mountain Views & Privacy on 10 Acres, holiday rental in Canaan

Beautiful 3 BR Berkshire Home - Mountain Views & Privacy on 10 Acres

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cabin on forest road, holiday rental in Canaan

Cabin on forest road

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, holiday rental in Canaan

Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautifully Restored 1820s Industrial Loft Living On A Creek, holiday rental in Canaan

Beautifully Restored 1820s Industrial Loft Living On A Creek

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND, holiday rental in Canaan

SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Historical Dutch Gem In The Hudson Valley, holiday rental in Canaan

Historical Dutch Gem In The Hudson Valley

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Family-friendly Cottage Near Lake, Tanglewood, holiday rental in Canaan

Family-friendly Cottage Near Lake, Tanglewood

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, holiday rental in Canaan

Sophisticated & Comfortable Stockbridge Retreat A+ Location Modern Amenities

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Morning Face - Berkshire estate with heated pool, views and privacy., holiday rental in Canaan

Morning Face - Berkshire estate with heated pool, views and privacy.

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Modern Retreat with Stunning Western Views, holiday rental in Canaan

Modern Retreat with Stunning Western Views

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Berkshire Blueberry Lodge LLC - Near Jiminy Peak, holiday rental in Canaan

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Long term availability Berkshire chalet with hot tub and fast WIFI, holiday rental in Canaan

Long term availability Berkshire chalet with hot tub and fast WIFI

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy & Modern Home -mins from Tanglewood & Kripalu, holiday rental in Canaan

Cozy & Modern Home -mins from Tanglewood & Kripalu

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly, holiday rental in Canaan

Relax in the Country - Peace, quiet and family friendly

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Home in Malden Bridge, Columbia County, New York, holiday rental in Canaan

The Home in Malden Bridge, Columbia County, New York

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Secluded Family-Friendly Home, holiday rental in Canaan

Secluded Family-Friendly Home

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bellavista Country Estate - The Library Suite, holiday rental in Canaan

Bellavista Country Estate - The Library Suite

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Pineview - Ideal Escape, holiday rental in Canaan

Pineview - Ideal Escape

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Berkshires Home w/Kayak - Walk to Stockbridge Bowl, holiday rental in Canaan

Berkshires Home w/Kayak - Walk to Stockbridge Bowl

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Meadow House 4 bdrm 4 bath house, holiday rental in Canaan

The Meadow House 4 bdrm 4 bath house

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Modern Cozy Wooded Retreat, holiday rental in Canaan

Modern Cozy Wooded Retreat

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Country estate on 100 acres perfect for families, holiday rental in Canaan

Country estate on 100 acres perfect for families

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Modern Condo for the Berkshires, holiday rental in Canaan

Cozy Modern Condo for the Berkshires

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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One of the Finest Homes and Best location in the Berkshires, holiday rental in Canaan

One of the Finest Homes and Best location in the Berkshires

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bellavista Country Estate - Rose Suite, holiday rental in Canaan

Bellavista Country Estate - Rose Suite

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Bellavista Country Estate, holiday rental in Canaan

Beautiful Bellavista Country Estate

8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, holiday rental in Canaan

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Berkshire Mountain Hideaway, holiday rental in Canaan

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hudson Valley Berkshires Cottage, holiday rental in Canaan

Hudson Valley Berkshires Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chalet near 4 ski resorts with hot tub, holiday rental in Canaan

Chalet near 4 ski resorts with hot tub

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - The Lodge's Campsite, holiday rental in Canaan

Tentrr Signature Site - The Lodge's Campsite

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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CABIN FEVER IN STOCKBRIDGE, holiday rental in Canaan

CABIN FEVER IN STOCKBRIDGE

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded House with Picturesque Views in Historic Old Chatham, NY, holiday rental in Canaan

Secluded House with Picturesque Views in Historic Old Chatham, NY

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Artist's Cottage on the Lake Mahkeenac, holiday rental in Canaan

Artist's Cottage on the Lake Mahkeenac

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private, Mountain Retreat with Indoor Pool and Fantastic Westward Mountain Views, holiday rental in Canaan

Private, Mountain Retreat with Indoor Pool and Fantastic Westward Mountain Views

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!, holiday rental in Canaan

NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stockbridge Bowl Lake Community, holiday rental in Canaan

Stockbridge Bowl Lake Community

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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