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Spencertown Holiday Rentals

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50 rentals in Spencertown.
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Modern Cozy Wooded Retreat, holiday rental in Spencertown

Modern Cozy Wooded Retreat

2 bedrooms
2 bathrooms
Sleeps 6
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Hudson Valley Berkshires Cottage, holiday rental in Spencertown

Hudson Valley Berkshires Cottage

2 bedrooms
2 bathrooms
Sleeps 4
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Beauty in the Berkshires, holiday rental in Spencertown

Beauty in the Berkshires

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Spring Break Special!  Stay two nights get one free for March and April!, holiday rental in Spencertown

Spring Break Special! Stay two nights get one free for March and April!

3 bedrooms
3 bathrooms
Sleeps 8
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Secluded and Private Location in the Mountains yet close to Skiing & attractions, holiday rental in Spencertown

Secluded and Private Location in the Mountains yet close to Skiing & attractions

4 bedrooms
3 bathrooms
Sleeps 8
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Berkshire Farmhouse Vacation, holiday rental in Spencertown

Berkshire Farmhouse Vacation

5 bedrooms
2 bathrooms
Sleeps 15
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Vacation in a  Berkshire Farmhouse, holiday rental in Spencertown

Vacation in a Berkshire Farmhouse

5 bedrooms
2 bathrooms
Sleeps 15
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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, holiday rental in Spencertown

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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2 bedroom Riverhouse in the Heart of the Berkshires, holiday rental in Spencertown

2 bedroom Riverhouse in the Heart of the Berkshires

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Farm House on beautiful old Horse Farm!!, holiday rental in Spencertown

Farm House on beautiful old Horse Farm!!

3 bedrooms
3 bathrooms
Sleeps 10
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., holiday rental in Spencertown

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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Charming, Quiet, Modern, Wooded, River Front, holiday rental in Spencertown

Charming, Quiet, Modern, Wooded, River Front

3 bedrooms
2 bathrooms
Sleeps 13
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Beautifully decorated & immaculate log chalet, holiday rental in Spencertown

Beautifully decorated & immaculate log chalet

3 bedrooms
2 bathrooms
Sleeps 6
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Charming Farmhouse Steps from Downtown West Stockbridge, holiday rental in Spencertown

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, holiday rental in Spencertown

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE, holiday rental in Spencertown

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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Peaceful Woodland Home in the Heart of the Berkshires, holiday rental in Spencertown

Peaceful Woodland Home in the Heart of the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quiet Guest House In The Green River Valley, holiday rental in Spencertown

Quiet Guest House In The Green River Valley

2 bedrooms
2 bathrooms
Sleeps 5
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Cabin on forest road, holiday rental in Spencertown

Cabin on forest road

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

Beautifully Restored 1820s Industrial Loft Living On A Creek

2 bedrooms
3 bathrooms
Sleeps 6
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Two Rooms with En-Suite in Quiet Woodland, holiday rental in Spencertown

Two Rooms with En-Suite in Quiet Woodland

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Case Mill-Secluded Berkshire farmhouse, mill, pond, waterfall, 28 acre forest., holiday rental in Spencertown

Case Mill-Secluded Berkshire farmhouse, mill, pond, waterfall, 28 acre forest.

3 bedrooms
2 bathrooms
Sleeps 7
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Private Hillsdale Home With Views Of Catamount., holiday rental in Spencertown

Private Hillsdale Home With Views Of Catamount.

3 bedrooms
3 bathrooms
Sleeps 6
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Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires, holiday rental in Spencertown

Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, holiday rental in Spencertown

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 Spencertown

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

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Upscale Country Cottage, holiday rental in Spencertown

Upscale Country Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Long term availability Berkshire chalet with hot tub and fast WIFI, holiday rental in Spencertown

Long term availability Berkshire chalet with hot tub and fast WIFI

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tranquil 3BR Stockbridge House w/Private Deck, holiday rental in Spencertown

Tranquil 3BR Stockbridge House w/Private Deck

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly, holiday rental in Spencertown

Relax in the Country - Peace, quiet and family friendly

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy apartment overlooking our small farm.  Family Friendly., holiday rental in Spencertown

Cozy apartment overlooking our small farm. Family Friendly.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Secluded House with Picturesque Views in Historic Old Chatham, NY, holiday rental in Spencertown

Secluded House with Picturesque Views in Historic Old Chatham, NY

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Berkshires Ski/Summer House, Great Views, holiday rental in Spencertown

Lakefront Berkshires Ski/Summer House, Great Views

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Family-Friendly Home, holiday rental in Spencertown

Secluded Family-Friendly Home

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hillhouse Log Cabin, holiday rental in Spencertown

Hillhouse Log Cabin

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Newly Renovated Colonial on the River! Sleeps 5-6, holiday rental in Spencertown

Newly Renovated Colonial on the River! Sleeps 5-6

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Vacation Home on 10 Acres with Pool and Spa, holiday rental in Spencertown

Vacation Home on 10 Acres with Pool and Spa

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Total Privacy! Tanglewood Retreat With Berkshire Views!, holiday rental in Spencertown

Total Privacy! Tanglewood Retreat With Berkshire Views!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Iris Room, holiday rental in Spencertown

Iris Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Horse Room, holiday rental in Spencertown

Horse Room

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautifully Renovated Berkshires Farmhouse, holiday rental in Spencertown

Beautifully Renovated Berkshires Farmhouse

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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One of the Finest Homes and Best location in the Berkshires, holiday rental in Spencertown

One of the Finest Homes and Best location in the Berkshires

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, holiday rental in Spencertown

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Berkshire Mountain Hideaway, holiday rental in Spencertown

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Chalet near 4 ski resorts with hot tub, holiday rental in Spencertown

Chalet near 4 ski resorts with hot tub

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious secluded  yet close to everything, holiday rental in Spencertown

Spacious secluded yet close to everything

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Winter Wonderland, minutes to Hudson and Berkshires, holiday rental in Spencertown

Winter Wonderland, minutes to Hudson and Berkshires

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tentrr Signature Site - WATER + WOODS, holiday rental in Spencertown

Tentrr Signature Site - WATER + WOODS

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - The Lodge's Campsite, holiday rental in Spencertown

Tentrr Signature Site - The Lodge's Campsite

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Contemporary With Beautiful Gardens, holiday rental in Spencertown

Spacious Contemporary With Beautiful Gardens

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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