Colebrook Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

46 Houses

12

Colebrook Dream

Connecticut / Colebrook

Colebrook house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$300

Price per night from

$300

Great rentals within 20 miles that match your search

Distance approx 15.57 km from Colebrook

(4) Excellent 

24

Waterfront Cottage - 10 Mins to Great Barrington!

Berkshires / New Marlborough

New Marlborough cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ski
  • Suitable for children age 5+

Price per night from

$180

Responds fast!
avg. 10 minutes

Price per night from

$180

Distance approx 14.97 km from Colebrook

(1) Excellent 

37

Charming 2+2 Lakeside Cottage on Best Lake in CT

Connecticut / Salisbury

Salisbury cottage

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$181

Price per night from

$181

Distance approx 19.27 km from Colebrook

(4) Excellent 

20

Escape to the Berkshires!

Berkshires / Becket

Becket house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$276

Price per night from

$276

Distance approx 18.31 km from Colebrook

(1) Excellent 

13

Lake House

Connecticut / Lakeville

Lakeville house

5 9 2 nights min

  • 5 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$601

Price per night from

$601

Distance approx 13.67 km from Colebrook

32

Berkshire Home on Lake Garfield w/Dock & Boats

Berkshires / Monterey

Monterey house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$301

Responds fast!
avg. 10 minutes

Price per night from

$301

Distance approx 15.56 km from Colebrook

24

Rustic Berkshires Cottage w/ Views of Lake Buel!

Berkshires / New Marlborough

New Marlborough cottage

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Pet Friendly

Price per night from

$110

Responds fast!
avg. 52 minutes

Price per night from

$110

Distance approx 17.72 km from Colebrook

(13) Very Good 

13

Quiet Comfortable Cabin 5 Min. Walk to Lake

Berkshires / Becket

Becket house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are
…see more

Price per night from

$150

Price per night from

$150

Distance approx 13.11 km from Colebrook

(1) Excellent 

20

Enjoy horses and the largest recreational lake in Massachusetts

Berkshires / East Otis

East Otis apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$110

Price per night from

$110

Distance approx 19.08 km from Colebrook

18

Spacious wooded home

Berkshires / Becket

Becket house

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Private garden

Price per night from

$196

Price per night from

$196

Distance approx 14.07 km from Colebrook

(1) Excellent 

11

Riverwood - Cozy Carriage House in the Woods

Connecticut / Falls Village

Falls Village apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Private garden

Price per night from

$226

Price per night from

$226

Distance approx 14.12 km from Colebrook

(19) Excellent 

18

The Cottage at Great Falls

Connecticut / Falls Village

Falls Village cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
“Relaxation Overload” Went with the girlfriend for a weekend getaway and chose the perfect place. Extremely relaxing and soothing trip. Everything you need is there, french press? Yep. Towels? Yep. Amazing art? Yep! This place is incredibly decorated a
…see more

Price per night from

$241

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$241

Distance approx 7.28 km from Colebrook Show on Map

24

Waterfront Home in Tolland w/ Deck - Steps to Lake

Connecticut / West Hartland

West Hartland log cabin

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$221

Responds fast!
avg. 10 minutes

Price per night from

$221

Distance approx 12.58 km from Colebrook

10

Country Victorian Serenity in the Berkshires

Berkshires / New Marlborough

New Marlborough house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Suitable for children age 5+
  • Private garden

Price per night from

$230

Price per night from

$230

Distance approx 13.29 km from Colebrook

(5) Excellent 

10

Apple Cottage

Berkshires / Sheffield

Sheffield farmhouse

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Ask about children
  • Air conditioning
  • Private garden

Price per night from

$376

Responds fast!
avg. 3 hours 22 minutes

Price per night from

$376

Distance approx 18.84 km from Colebrook

24

Prana Residence - Spa

Connecticut / Cornwall Bridge

Cornwall Bridge house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$751

Price per night from

$751

Distance approx 15.01 km from Colebrook

23

Spacious Lakeside Berkshire Home

Berkshires / Monterey

Monterey house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$401

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$401

Distance approx 19.31 km from Colebrook

(1) Excellent 

10

Romantic Berkshire Cottage on Storybook Estate

Berkshires / Tyringham

Tyringham cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$226

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$226

Distance approx 14.34 km from Colebrook

24

Beautiful Lakefront Berkshire Rental

Berkshires / Monterey

Monterey house

5 6 7 nights min

  • 5 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$422

Responds fast!
avg. 3 hours 51 minutes

Price per night from

$422

Distance approx 13.42 km from Colebrook

22

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Berkshires / Otis

Otis house

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$601

Price per night from

$601

Distance approx 16.51 km from Colebrook

12

Fabulous Post & Beam Berkshire Rental

Berkshires / Monterey

Monterey house

7 21 nights min

  • sleeps 7
  • 21 nights min
  • Ask about children
  • Car not necessary
  • Ask about pets

Price per night from

$180

Price per night from

$180

Distance approx 18.36 km from Colebrook

6

Berkshires on the Pond

Berkshires / Becket

Becket house

2 2 4 nights min

  • 2 bedrooms
  • sleeps 2
  • 4 nights min
  • Nearest beach 16 mi
  • Ask about children
  • Private garden

Price per night from

$126

Price per night from

$126

Distance approx 16.32 km from Colebrook

(1) Excellent 

21

Three-bedroom one-and-a-half bath ranch with lots of room inside and outside

Connecticut / Granby

Granby house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$150

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$150

Distance approx 19.31 km from Colebrook

9

Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

Berkshires / Tyringham

Tyringham house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Ask about children
  • Ask about pets

Price per night from

$251

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$251

Distance approx 6.85 km from Colebrook Show on Map

20

Beautiful Lake House - Magnificent in all 4 Seasons 3 Bed, 2 Bath

Connecticut / Winsted

Winsted house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$225

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$225

Distance approx 13.36 km from Colebrook

24

Cozy Canton Home w/Porch & Sauna Near Ski Sundown!

Connecticut / Canton

Canton house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$155

Responds fast!
avg. 53 minutes

Price per night from

$155

Distance approx 13.41 km from Colebrook

44

COMFY COZY 5 BEDROOM HOME - 2 WOODED PRIVATE ACRES

Connecticut / Hartford

Hartford house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$396

Price per night from

$396

Distance approx 12.25 km from Colebrook

35

Charming Private Guest Suite in Historic Village in the Berkshires

Berkshires / New Marlborough

New Marlborough studio

Studio 2 1 night min

  • Studio
  • sleeps 2
  • 1 night min

Price per night from

$96

Price per night from

$96

Distance approx 15.83 km from Colebrook

13

Quiet Country Contemporary Home on 5 Private Acres

Connecticut / West Cornwall

West Cornwall house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 6 mi
  • Child Friendly
  • Air conditioning

Price per night from

$406

Price per night from

$406

Distance approx 11.93 km from Colebrook

24

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

Berkshires / Otis

Otis log cabin

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$100

Responds fast!
avg. 52 minutes

Price per night from

$100

Distance approx 15.12 km from Colebrook

(1) Excellent 

14

The perfect Southern Berkshire winter vacation esc

Berkshires / Sheffield

Sheffield house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$501

Price per night from

$501

Distance approx 18.96 km from Colebrook

30

NEW! Becket Home on 11 Acres w/ Swimming Pond!

Berkshires / Becket

Becket house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$326

Responds fast!
avg. 10 minutes

Price per night from

$326

Distance approx 14.15 km from Colebrook

16

Direct Waterfront Lake Home on Tranquil Harwinton

Connecticut / Harwinton

Harwinton cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$225

Price per night from

$225

Distance approx 13.8 km from Colebrook

17

Picturesque 19th century home on 3 private acres

Berkshires / New Marlborough

New Marlborough house

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$151

Price per night from

$151

Distance approx 18.64 km from Colebrook

(12) Excellent 

17

Serene Lakefront Cottage

Berkshires / Becket

Becket house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Peaceful country escape” Really enjoyed the stay here. Very complete driving and house directions provided by the owners, and checking in - even at a late hour - was a breeze. The house was very clean, woods and lake were beautiful. Many of the hou
…see more

Price per night from

$145

Price per night from

$145

Distance approx 16.78 km from Colebrook

12

Cottage on East Twin Lakes, Internet Access, A/C.

Connecticut / Salisbury

Salisbury cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$157

Price per night from

$157

Distance approx 12.41 km from Colebrook

31

Connecticut Wine Country Getaway!

Connecticut / North Granby

North Granby apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$116

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$116

Distance approx 15.34 km from Colebrook

(3) Very Good 

22

Comfortable Rustic Cottage on 4 Wooded Acres with Brook

Connecticut / West Cornwall

West Cornwall cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 12 mi
  • Child Friendly
  • Air conditioning

Price per night from

$150

Price per night from

$150