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Colebrook Holiday Rentals

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49 rentals in Colebrook.
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Colebrook Dream, holiday rental in Colebrook

Colebrook Dream

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Room to Roam. Modern home with all amenities + sep. cabin on 10+  wooded acres., holiday rental in Colebrook

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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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., holiday rental in Colebrook

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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TRANQUIL private home with garden OASIS and heated POOL, holiday rental in Colebrook

TRANQUIL private home with garden OASIS and heated POOL

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious family home tucked away in a rural, friendly, lake community!, holiday rental in Colebrook

Spacious family home tucked away in a rural, friendly, lake community!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious waterfront Berkshire home family private get-away, holiday rental in Colebrook

Spacious waterfront Berkshire home family private get-away

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Southfield Village!, holiday rental in Colebrook

Beautiful Southfield Village!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious rural get away, holiday rental in Colebrook

Luxurious rural get away

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Spacious Country Retreat With Secluded Tree Top Mountain Views, holiday rental in Colebrook

Spacious Country Retreat With Secluded Tree Top Mountain Views

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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North Canaan's Quiet & Cozy Home, holiday rental in Colebrook

North Canaan's Quiet & Cozy Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic home located on scenic Farmington River., holiday rental in Colebrook

Historic home located on scenic Farmington River.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Little House in the Woods, holiday rental in Colebrook

The Little House in the Woods

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake Community - Near Town, Attractions, holiday rental in Colebrook

Lake Community - Near Town, Attractions

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Cottage at Great Falls, holiday rental in Colebrook

The Cottage at Great Falls

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming cedar shingle cottage, holiday rental in Colebrook

Charming cedar shingle cottage

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Beautiful Farm House Located On 12 Acres Of Farm Property., holiday rental in Colebrook

Beautiful Farm House Located On 12 Acres Of Farm Property.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions, holiday rental in Colebrook

Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington., holiday rental in Colebrook

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire lake house on lake Garfield, Monterey MA; private, 4 BR, sleeps 10, holiday rental in Colebrook

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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Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property., holiday rental in Colebrook

Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property.

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Sunset Place - Modern Lake House on Otis Reservoir - 5 Night Min Stay - Sleeps 6, holiday rental in Colebrook

Sunset Place - Modern Lake House on Otis Reservoir - 5 Night Min Stay - Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Direct Waterfront with Private Beach - Entire Home, holiday rental in Colebrook

Direct Waterfront with Private Beach - Entire Home

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, holiday rental in Colebrook

Lakeridge Litchfield Resort Townhome Pool Tennis Skiing

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Converted Berkshire schoolhouse on a quiet river, holiday rental in Colebrook

Converted Berkshire schoolhouse on a quiet river

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Family Friendly Farmhouse in the Berkshires, holiday rental in Colebrook

Family Friendly Farmhouse in the Berkshires

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Modern Farmhouse in the Southern Berkshires, holiday rental in Colebrook

Modern Farmhouse in the Southern Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Ashley Falls Cottage Retreat, holiday rental in Colebrook

Charming Ashley Falls Cottage Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lake House on the Cleanest Lake in CT, holiday rental in Colebrook

Lake House on the Cleanest Lake in CT

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming 2+2 Lakeside Cottage on Best Lake in CT, holiday rental in Colebrook

Charming 2+2 Lakeside Cottage on Best Lake in CT

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy horses and the largest recreational lake in Massachusetts, holiday rental in Colebrook

Enjoy horses and the largest recreational lake in Massachusetts

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Lakefront Escape w/ Private Dock & Kayaks, holiday rental in Colebrook

NEW! Lakefront Escape w/ Private Dock & Kayaks

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Berkshire Home in Private Community, holiday rental in Colebrook

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 Colebrook

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

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES, holiday rental in Colebrook

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Lakefront Berkshire Rental, holiday rental in Colebrook

Beautiful Lakefront Berkshire Rental

5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake House  - Direct Waterfront, Immaculate; charming all 4 seasons, holiday rental in Colebrook

Lake House - Direct Waterfront, Immaculate; charming all 4 seasons

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Lakeside Berkshire Home, holiday rental in Colebrook

Spacious Lakeside Berkshire Home

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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East Otis Reservoir Cabin w/ Porch - Walk to Lake!, holiday rental in Colebrook

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Monterey Home w/ Porch: Walk to Lake Garfield, holiday rental in Colebrook

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern Goshen House w/ Deck, Backyard & Views, holiday rental in Colebrook

Modern Goshen House w/ Deck, Backyard & Views

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Echo Hill, holiday rental in Colebrook

Tentrr Signature Site - Echo Hill

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Maple Corner Farm's Meadow Site, holiday rental in Colebrook

Tentrr Signature Site - Maple Corner Farm's Meadow Site

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Quaint Quiet Serene !!, holiday rental in Colebrook

Quaint Quiet Serene !!

1 bedroom
0 bathrooms
Sleeps 4
Match: Sleeps
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Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns, holiday rental in Colebrook

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 Colebrook

Konkapot Cottage, Pastoral Bliss With Wide Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! East Otis Romantic Cottage w/ Deck & BBQ!, holiday rental in Colebrook

NEW! East Otis Romantic Cottage w/ Deck & BBQ!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Camping in the Woods of the Berkshires, holiday rental in Colebrook

Tentrr Signature Site - Camping in the Woods of the Berkshires

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ski Retreat -- Private Modern on 40 Acres of Land, holiday rental in Colebrook

Ski Retreat -- Private Modern on 40 Acres of Land

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Spectacular Fall Foliage in Sheffield  with Monthly Special Pricing Available, holiday rental in Colebrook

Spectacular Fall Foliage in Sheffield with Monthly Special Pricing Available

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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