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Holiday Rentals in Monterey

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50 rentals in Monterey.
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Gorgeous Log Cabin in the Berkshires, holiday rental in Monterey

Gorgeous Log Cabin in the Berkshires

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!, holiday rental in Monterey

Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn, holiday rental in Monterey

Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Berkshire lake house on lake Garfield, Monterey MA; private, 4 BR, sleeps 10, holiday rental in Monterey

Berkshire lake house on lake Garfield, Monterey MA; private, 4 BR, sleeps 10

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, holiday rental in Monterey

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Berkshire Mountains Cabin, holiday rental in Monterey

Amazing Berkshire Mountains Cabin

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Spacious Lakeside Berkshire Home, holiday rental in Monterey

Spacious Lakeside Berkshire Home

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Pet-Friendly Berkshires Home w/Dock & Fire Pit!, holiday rental in Monterey

Pet-Friendly Berkshires Home w/Dock & Fire Pit!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Lakefront Berkshire Rental, holiday rental in Monterey

Beautiful Lakefront Berkshire Rental

5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Monterey Home w/ Porch: Walk to Lake Garfield, holiday rental in Monterey

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fabulous Post & Beam Berkshire Rental, holiday rental in Monterey

Fabulous Post & Beam Berkshire Rental

0 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Room to Roam. Modern home with all amenities + sep. cabin on 10+  wooded acres., holiday rental in Monterey

Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private rustic cottage with lake access, holiday rental in Monterey

Private rustic cottage with lake access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND  near TANGLEWOOD, holiday rental in Monterey

PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!, holiday rental in Monterey

The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., holiday rental in Monterey

Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Downtown GB apartment walk to shops and restaurants, holiday rental in Monterey

Downtown GB apartment walk to shops and restaurants

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Southfield Village!, holiday rental in Monterey

Beautiful Southfield Village!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern Secluded Home In Wooded Setting, holiday rental in Monterey

Modern Secluded Home In Wooded Setting

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lake Community - Near Town, Attractions, holiday rental in Monterey

Lake Community - Near Town, Attractions

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS, holiday rental in Monterey

Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Scenic ByWay Waterfront Property, holiday rental in Monterey

Scenic ByWay Waterfront Property

3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!, holiday rental in Monterey

Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More, holiday rental in Monterey

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style, holiday rental in Monterey

Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Barn Apartment in Gorgeous Stonybrook Farm, holiday rental in Monterey

Barn Apartment in Gorgeous Stonybrook Farm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gem of the Berkshires, walk to downtown & lake., holiday rental in Monterey

Gem of the Berkshires, walk to downtown & lake.

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood, holiday rental in Monterey

Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Rabbit Run - in the heart of Stockbridge, holiday rental in Monterey

Rabbit Run - in the heart of Stockbridge

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington., holiday rental in Monterey

Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Farmhouse in the Southern Berkshires, holiday rental in Monterey

Modern Farmhouse in the Southern Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern Victorian on the Hill, holiday rental in Monterey

Modern Victorian on the Hill

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!, holiday rental in Monterey

Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut, holiday rental in Monterey

Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful Berkshire Home in Private Community, holiday rental in Monterey

Beautiful Berkshire Home in Private Community

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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'The Mill River Cabin’ w/ Fireplace & River View!, holiday rental in Monterey

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

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Berkshires- Full First Floor Guest Suite in Historic NE Village, holiday rental in Monterey

Berkshires- Full First Floor Guest Suite in Historic NE Village

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tanglewood / Berkshires - 2 Bed 2 Bath Apartment, holiday rental in Monterey

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Deluxe New Home, 2 Master Suites, Tanglewood Area, holiday rental in Monterey

Deluxe New Home, 2 Master Suites, Tanglewood Area

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES, holiday rental in Monterey

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Private Home Overlooking Stevens Lake, holiday rental in Monterey

Private Home Overlooking Stevens Lake

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr, holiday rental in Monterey

NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Echo Hill, holiday rental in Monterey

Tentrr Signature Site - Echo Hill

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Running Spring Farm, holiday rental in Monterey

Tentrr Signature Site - Running Spring Farm

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Converted Berkshire schoolhouse on a quiet river, holiday rental in Monterey

Converted Berkshire schoolhouse on a quiet river

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns, holiday rental in Monterey

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns

6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Konkapot Cottage, Pastoral Bliss With Wide Views, holiday rental in Monterey

Konkapot Cottage, Pastoral Bliss With Wide Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More, holiday rental in Monterey

Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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NEW! Cozy Great Barrington Home 1 Mi to Ski Resort, holiday rental in Monterey

NEW! Cozy Great Barrington Home 1 Mi to Ski Resort

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Tentrr Signature Site - Camping in the Woods of the Berkshires, holiday rental in Monterey

Tentrr Signature Site - Camping in the Woods of the Berkshires

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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