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Colebrook Holiday Rentals

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Bedrooms

Bathrooms

Amenities

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Distance from

5 mi
50 rentals in Colebrook.
Unique & extraordinary experience - renew your senses. Delightful waterfront!, holiday rental in Colebrook
Unique & extraordinary experience - renew your senses. Delightful waterfront!, holiday rental in Colebrook
Unique & extraordinary experience - renew your senses. Delightful waterfront!, holiday rental in Colebrook

Unique & extraordinary experience - renew your senses. Delightful waterfront!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stylish Comfort in a Stunning Country Setting, holiday rental in Colebrook
Stylish Comfort in a Stunning Country Setting, holiday rental in Colebrook
Stylish Comfort in a Stunning Country Setting, holiday rental in Colebrook

Stylish Comfort in a Stunning Country Setting

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The following properties within 20 miles of Colebrook match all your filters:
Enjoy a restful stay with fast internet, smart TV and the company of your pet., holiday rental in Colebrook
Enjoy a restful stay with fast internet, smart TV and the company of your pet., holiday rental in Colebrook
Enjoy a restful stay with fast internet, smart TV and the company of your pet., holiday rental in Colebrook

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Romantic weekend getaway!, holiday rental in Colebrook
Romantic weekend getaway!, holiday rental in Colebrook
Romantic weekend getaway!, holiday rental in Colebrook

Romantic weekend getaway!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!, holiday rental in Colebrook
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!, holiday rental in Colebrook
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!, holiday rental in Colebrook

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home, holiday rental in Colebrook
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home, holiday rental in Colebrook
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home, holiday rental in Colebrook

5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Romantic and Secluded Berkshire's Gem, holiday rental in Colebrook
Romantic and Secluded Berkshire's Gem, holiday rental in Colebrook
Romantic and Secluded Berkshire's Gem, holiday rental in Colebrook

Romantic and Secluded Berkshire's Gem

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Very charming house , that will make you feel like home, holiday rental in Colebrook
Very charming house , that will make you feel like home, holiday rental in Colebrook
Very charming house , that will make you feel like home, holiday rental in Colebrook

Very charming house , that will make you feel like home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct., holiday rental in Colebrook
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct., holiday rental in Colebrook
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct., holiday rental in Colebrook

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock, holiday rental in Colebrook
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock, holiday rental in Colebrook
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock, holiday rental in Colebrook

The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cabin in the Berkshires, holiday rental in Colebrook
Cozy Cabin in the Berkshires, holiday rental in Colebrook
Cozy Cabin in the Berkshires, holiday rental in Colebrook

Cozy Cabin in the Berkshires

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Our Cottage - Small in size, Big in character, On beautiful Highland Lake, holiday rental in Colebrook
Our Cottage - Small in size, Big in character, On beautiful Highland Lake, holiday rental in Colebrook
Our Cottage - Small in size, Big in character, On beautiful Highland Lake, holiday rental in Colebrook

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront Tranquility/Fishermans Delight, holiday rental in Colebrook
Lakefront Tranquility/Fishermans Delight, holiday rental in Colebrook
Lakefront Tranquility/Fishermans Delight, holiday rental in Colebrook

Lakefront Tranquility/Fishermans Delight

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, holiday rental in Colebrook
Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, holiday rental in Colebrook
Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, holiday rental in Colebrook

Lakeridge Litchfield Resort Townhome Pool Tennis Skiing

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Cottage at Highland Lake, year-round, waterfront with a boat dock, holiday rental in Colebrook
The Cottage at Highland Lake, year-round, waterfront with a boat dock, holiday rental in Colebrook
The Cottage at Highland Lake, year-round, waterfront with a boat dock, holiday rental in Colebrook

The Cottage at Highland Lake, year-round, waterfront with a boat dock

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock, holiday rental in Colebrook
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock, holiday rental in Colebrook
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock, holiday rental in Colebrook

The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Fall 2024! Cozy WATERFRONT Cottage on Highland Lake,  CT - central a/c and, holiday rental in Colebrook
Fall 2024! Cozy WATERFRONT Cottage on Highland Lake,  CT - central a/c and, holiday rental in Colebrook
Fall 2024! Cozy WATERFRONT Cottage on Highland Lake,  CT - central a/c and, holiday rental in Colebrook

Fall 2024! Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c and

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely 3 Bedroom Townhouse , perfect for skiing, holiday rental in Colebrook
Lovely 3 Bedroom Townhouse , perfect for skiing, holiday rental in Colebrook
Lovely 3 Bedroom Townhouse , perfect for skiing, holiday rental in Colebrook

Lovely 3 Bedroom Townhouse , perfect for skiing

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Berkshire classic home nestled in a quiet peaceful area, holiday rental in Colebrook
Beautiful Berkshire classic home nestled in a quiet peaceful area, holiday rental in Colebrook
Beautiful Berkshire classic home nestled in a quiet peaceful area, holiday rental in Colebrook

Beautiful Berkshire classic home nestled in a quiet peaceful area

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air, holiday rental in Colebrook
Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air, holiday rental in Colebrook
Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air, holiday rental in Colebrook

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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4 Bedroom Family Friendly Home in Riverton Paradise, holiday rental in Colebrook
4 Bedroom Family Friendly Home in Riverton Paradise, holiday rental in Colebrook
4 Bedroom Family Friendly Home in Riverton Paradise, holiday rental in Colebrook

4 Bedroom Family Friendly Home in Riverton Paradise

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Spacious Home nestled along the Blackberry River in Northwest CT, holiday rental in Colebrook
Spacious Home nestled along the Blackberry River in Northwest CT, holiday rental in Colebrook
Spacious Home nestled along the Blackberry River in Northwest CT, holiday rental in Colebrook

Spacious Home nestled along the Blackberry River in Northwest CT

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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sweet dreams retreat, holiday rental in Colebrook
sweet dreams retreat, holiday rental in Colebrook
sweet dreams retreat, holiday rental in Colebrook

sweet dreams retreat

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!, holiday rental in Colebrook
Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!, holiday rental in Colebrook
Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!, holiday rental in Colebrook

Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Great Family Cabin in the woods on a lake., holiday rental in Colebrook
Great Family Cabin in the woods on a lake., holiday rental in Colebrook
Great Family Cabin in the woods on a lake., holiday rental in Colebrook

Great Family Cabin in the woods on a lake.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., holiday rental in Colebrook
1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., holiday rental in Colebrook
1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., holiday rental in Colebrook

1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Canaan Valley Home, A Berkshires Getaway, holiday rental in Colebrook
Canaan Valley Home, A Berkshires Getaway, holiday rental in Colebrook
Canaan Valley Home, A Berkshires Getaway, holiday rental in Colebrook

Canaan Valley Home, A Berkshires Getaway

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., holiday rental in Colebrook
Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., holiday rental in Colebrook
Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., holiday rental in Colebrook

Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Iconic Cabin in the Berkshires, holiday rental in Colebrook
Iconic Cabin in the Berkshires, holiday rental in Colebrook
Iconic Cabin in the Berkshires, holiday rental in Colebrook

Iconic Cabin in the Berkshires

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Family House On Highland Lake with Dock, holiday rental in Colebrook
Family House On Highland Lake with Dock, holiday rental in Colebrook
Family House On Highland Lake with Dock, holiday rental in Colebrook

Family House On Highland Lake with Dock

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Lakefront Retreat at Porcupine Place, holiday rental in Colebrook
Lakefront Retreat at Porcupine Place, holiday rental in Colebrook
Lakefront Retreat at Porcupine Place, holiday rental in Colebrook

Lakefront Retreat at Porcupine Place

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!, holiday rental in Colebrook
Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!, holiday rental in Colebrook
Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!, holiday rental in Colebrook

Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford, holiday rental in Colebrook
Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford, holiday rental in Colebrook
Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford, holiday rental in Colebrook

Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Relax And Enjoy A Fun Getaway At The Bacchus Cottage!, holiday rental in Colebrook
Relax And Enjoy A Fun Getaway At The Bacchus Cottage!, holiday rental in Colebrook
Relax And Enjoy A Fun Getaway At The Bacchus Cottage!, holiday rental in Colebrook

Relax And Enjoy A Fun Getaway At The Bacchus Cottage!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cottage is currently rented for the year, and not available until further notice, holiday rental in Colebrook
Cottage is currently rented for the year, and not available until further notice, holiday rental in Colebrook
Cottage is currently rented for the year, and not available until further notice, holiday rental in Colebrook

Cottage is currently rented for the year, and not available until further notice

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!, holiday rental in Colebrook
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!, holiday rental in Colebrook
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!, holiday rental in Colebrook

Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 3-bedroom Modern cottage with lakeside views, holiday rental in Colebrook
Charming 3-bedroom Modern cottage with lakeside views, holiday rental in Colebrook
Charming 3-bedroom Modern cottage with lakeside views, holiday rental in Colebrook

Charming 3-bedroom Modern cottage with lakeside views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Spacious 4-bedroom condo with AC and WiFi in Litchfield County, holiday rental in Colebrook
Spacious 4-bedroom condo with AC and WiFi in Litchfield County, holiday rental in Colebrook
Spacious 4-bedroom condo with AC and WiFi in Litchfield County, holiday rental in Colebrook

Spacious 4-bedroom condo with AC and WiFi in Litchfield County

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Spacious Tolland Home w/ Deck + Screened Porch!, holiday rental in Colebrook
Spacious Tolland Home w/ Deck + Screened Porch!, holiday rental in Colebrook
Spacious Tolland Home w/ Deck + Screened Porch!, holiday rental in Colebrook

Spacious Tolland Home w/ Deck + Screened Porch!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tolland Cabin w/ Private Hot Tub & Grill!, holiday rental in Colebrook
Tolland Cabin w/ Private Hot Tub & Grill!, holiday rental in Colebrook
Tolland Cabin w/ Private Hot Tub & Grill!, holiday rental in Colebrook

Tolland Cabin w/ Private Hot Tub & Grill!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Book Your Perfect Fall Stay in the Berkshire Woods, holiday rental in Colebrook
Book Your Perfect Fall Stay in the Berkshire Woods, holiday rental in Colebrook
Book Your Perfect Fall Stay in the Berkshire Woods, holiday rental in Colebrook

Book Your Perfect Fall Stay in the Berkshire Woods

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serenity Summit: Hot Tub, Mountain Views, Book Now, holiday rental in Colebrook
Serenity Summit: Hot Tub, Mountain Views, Book Now, holiday rental in Colebrook
Serenity Summit: Hot Tub, Mountain Views, Book Now, holiday rental in Colebrook

Serenity Summit: Hot Tub, Mountain Views, Book Now

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful retreat in a lake community to the enjoy the summer season., holiday rental in Colebrook
Beautiful retreat in a lake community to the enjoy the summer season., holiday rental in Colebrook
Beautiful retreat in a lake community to the enjoy the summer season., holiday rental in Colebrook

Beautiful retreat in a lake community to the enjoy the summer season.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury on the River*Fish Camp-Close to Tanglewood, holiday rental in Colebrook
Luxury on the River*Fish Camp-Close to Tanglewood, holiday rental in Colebrook
Luxury on the River*Fish Camp-Close to Tanglewood, holiday rental in Colebrook

Luxury on the River*Fish Camp-Close to Tanglewood

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 2-bedroom apartment with AC, WiFi LAKE VIEWS!, holiday rental in Colebrook
Charming 2-bedroom apartment with AC, WiFi LAKE VIEWS!, holiday rental in Colebrook
Charming 2-bedroom apartment with AC, WiFi LAKE VIEWS!, holiday rental in Colebrook

Charming 2-bedroom apartment with AC, WiFi LAKE VIEWS!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private, lake community house in the serene Berkshire Foothills with pool table, holiday rental in Colebrook
Private, lake community house in the serene Berkshire Foothills with pool table, holiday rental in Colebrook
Private, lake community house in the serene Berkshire Foothills with pool table, holiday rental in Colebrook

Private, lake community house in the serene Berkshire Foothills with pool table

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Relax or be active! The choice is yours in this pet-friendly family home., holiday rental in Colebrook
Relax or be active! The choice is yours in this pet-friendly family home., holiday rental in Colebrook
Relax or be active! The choice is yours in this pet-friendly family home., holiday rental in Colebrook

Relax or be active! The choice is yours in this pet-friendly family home.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming 2-bedroom apartment in welcoming Winsted with WiFi, AC, holiday rental in Colebrook
Charming 2-bedroom apartment in welcoming Winsted with WiFi, AC, holiday rental in Colebrook
Charming 2-bedroom apartment in welcoming Winsted with WiFi, AC, holiday rental in Colebrook

Charming 2-bedroom apartment in welcoming Winsted with WiFi, AC

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakeside Cottage in the Berkshires, holiday rental in Colebrook
Lakeside Cottage in the Berkshires, holiday rental in Colebrook
Lakeside Cottage in the Berkshires, holiday rental in Colebrook

Lakeside Cottage in the Berkshires

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Home w/ Hot Tub in a Private Lake Community, holiday rental in Colebrook
Beautiful Home w/ Hot Tub in a Private Lake Community, holiday rental in Colebrook
Beautiful Home w/ Hot Tub in a Private Lake Community, holiday rental in Colebrook

Beautiful Home w/ Hot Tub in a Private Lake Community

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 50
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