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New Lebanon Holiday Rentals

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50 rentals in New Lebanon.
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Modern Retreat with Stunning Western Views, holiday rental in New Lebanon

Modern Retreat with Stunning Western Views

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Recently renovated 4 bedroom lakefront house in The Berkshires., holiday rental in New Lebanon

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, holiday rental in New Lebanon

New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, holiday rental in New Lebanon

Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, holiday rental in New Lebanon

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, holiday rental in New Lebanon

A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., holiday rental in New Lebanon

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., holiday rental in New Lebanon

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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Tranquil Lake House Getaway on Onota Lake, holiday rental in New Lebanon

Tranquil Lake House Getaway on Onota Lake

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Berkshire Lake House Vacation Rental, holiday rental in New Lebanon

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, holiday rental in New Lebanon

Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Waterfront home with deep water dock on Onota Lake, holiday rental in New Lebanon

Beautiful Waterfront home with deep water dock on Onota Lake

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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5 STAR! Lenox. Luxury. Location., holiday rental in New Lebanon

5 STAR! Lenox. Luxury. Location.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b, holiday rental in New Lebanon

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

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!, holiday rental in New Lebanon

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak, holiday rental in New Lebanon

Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Charming Farmhouse Steps from Downtown West Stockbridge, holiday rental in New Lebanon

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Grand Colonial Home in the Heart of The Berkshires, holiday rental in New Lebanon

Grand Colonial Home in the Heart of The Berkshires

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Home in the Berkshires, holiday rental in New Lebanon

Home in the Berkshires

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

The Home in Malden Bridge, Columbia County, New York

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Cabin on forest road, holiday rental in New Lebanon

Cabin on forest road

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, holiday rental in New Lebanon

6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND, holiday rental in New Lebanon

SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Berkshire Getaway with Scenic Lake Views & Access, holiday rental in New Lebanon

Charming Berkshire Getaway with Scenic Lake Views & Access

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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A MAGIC SPOT: Booking Fall and the Ski Season now!, holiday rental in New Lebanon

A MAGIC SPOT: Booking Fall and the Ski Season now!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Morning Face - Berkshire estate with heated pool, views and privacy., holiday rental in New Lebanon

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

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Exquisite Apartment in Grand Victorian Home 1, holiday rental in New Lebanon

Exquisite Apartment in Grand Victorian Home 1

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded House with Picturesque Views in Historic Old Chatham, NY, holiday rental in New Lebanon

Secluded House with Picturesque Views in Historic Old Chatham, NY

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Long term availability Berkshire chalet with hot tub and fast WIFI, holiday rental in New Lebanon

Long term availability Berkshire chalet with hot tub and fast WIFI

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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6BR Berkshire Bliss - 38 private acres - close to skiing and town, holiday rental in New Lebanon

6BR Berkshire Bliss - 38 private acres - close to skiing and town

6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly, holiday rental in New Lebanon

Relax in the Country - Peace, quiet and family friendly

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, holiday rental in New Lebanon

Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Family-Friendly Home, holiday rental in New Lebanon

Secluded Family-Friendly Home

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Whitman Woods - A Berkshire Vacation, holiday rental in New Lebanon

Whitman Woods - A Berkshire Vacation

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Restored 1881 Farm House, holiday rental in New Lebanon

Restored 1881 Farm House

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bentley/Wyndham Hancock Mass at Jiminy Peak, holiday rental in New Lebanon

Bentley/Wyndham Hancock Mass at Jiminy Peak

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite Apartment in Grand Victorian 2, holiday rental in New Lebanon

Exquisite Apartment in Grand Victorian 2

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Meadow House 4 bdrm 4 bath house, holiday rental in New Lebanon

The Meadow House 4 bdrm 4 bath house

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Christmas in The Berkshires, holiday rental in New Lebanon

Christmas in The Berkshires

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Thanksgiving week lux condo/4 Berkshires, holiday rental in New Lebanon

Thanksgiving week lux condo/4 Berkshires

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, holiday rental in New Lebanon

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

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, holiday rental in New Lebanon

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, holiday rental in New Lebanon

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 New Lebanon

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Round Mountain Camp, holiday rental in New Lebanon

Tentrr Signature Site - Round Mountain Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Chalet near 4 ski resorts with hot tub, holiday rental in New Lebanon

Chalet near 4 ski resorts with hot tub

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, holiday rental in New Lebanon

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - The Lodge's Campsite, holiday rental in New Lebanon

Tentrr Signature Site - The Lodge's Campsite

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Apartment Newly Remodeled Super Location, holiday rental in New Lebanon

Apartment Newly Remodeled Super Location

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Lakeside Berkshires Home Near Hiking & Skiing, holiday rental in New Lebanon

NEW! Lakeside Berkshires Home Near Hiking & Skiing

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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