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158 Houses

9

Cedar Chest

New York / Canaan

Canaan cottage

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Air conditioning

Price per night from

$100

Price per night from

$100

Great rentals within 20 miles that match your search

Distance approx 7.05 km from Canaan

(4) Excellent 

10

Great Vacation House in the Berkshires on Richmond Pond

Berkshires / Richmond

Richmond house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$186

Price per night from

$186

Distance approx 12.07 km from Canaan

19

Relax Like Royalty in Your Own Castle!

New York / Ghent

Ghent house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$298

Price per night from

$298

Distance approx 9.02 km from Canaan

18

Mountain Views Atop Blueberry Hill on 40 Acres

New York / Austerlitz

Austerlitz house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$200

Price per night from

$200

Distance approx 11.86 km from Canaan

(1) Excellent 

17

Restored 1886 Eyebrow Colonial

Berkshires / Stockbridge

Stockbridge house

2 6 7 nights min

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

Price per night from

$214

Price per night from

$214

Distance approx 12.65 km from Canaan

24

Cozy Jiminy Peak Area Condo w/Patio & Pool Access!

Berkshires / Hancock

Hancock apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$185

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$185

Distance approx 10.73 km from Canaan

31

Big Beautiful 7 bedroom 3 bath hot tub pool table

Berkshires / Pittsfield

Pittsfield house

7 18 2 nights min

  • 7 bedrooms
  • sleeps 18
  • 2 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$299

Price per night from

$299

Distance approx 18.22 km from Canaan

46

Hudson River Villa w/Pool, Spa & Private Beach!

Catskill Region / Athens

Athens villa

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$897

Responds fast!
avg. 42 minutes

Price per night from

$897

Distance approx 19.37 km from Canaan

31

Lakefront house , great lake and mountain views

Catskill Region / Athens

Athens house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$312

Price per night from

$312

Distance approx 17.52 km from Canaan

18

Historic Home on 8.5 Acres

Berkshires / Dalton

Dalton house

3 9 3 nights min

  • 3 bedrooms
  • sleeps 9
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$399

Price per night from

$399

Distance approx 15.41 km from Canaan

(17) Excellent 

31

Beautifully decorated & immaculate log chalet

New York / Hillsdale

Hillsdale log cabin

3 6 2 nights min

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

Price per night from

$175

Price per night from

$175

Distance approx 15.64 km from Canaan

28

Country Retreat w/ Pool Near Hip Hudson, NY

New York / Hudson

Hudson house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Ask about pets

Price per night from

$399

Price per night from

$399

Distance approx 13.15 km from Canaan

(2) Excellent 

24

Country Elegance in the Berkshires

Berkshires / Great Barrington

Great Barrington house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$648

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$648

Distance approx 11.33 km from Canaan

48

Total Privacy! Tanglewood Retreat With Berkshire Views!

New York / Hillsdale

Hillsdale house

5 14 2 nights min

  • 5 bedrooms
  • sleeps 14
  • 2 nights min
  • Ask about children

Price per night from

$598

Price per night from

$598

Distance approx 12.88 km from Canaan

(2) Average 

27

Shaker Hill

Berkshires / Great Barrington

Great Barrington house

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$374

Responds fast!
avg. 56 minutes

Price per night from

$374

Distance approx 14.66 km from Canaan

(17) Excellent 

10

Stone School Cottage

Berkshires / Lanesboro

Lanesboro cottage

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden
“A wonderful experience” My parents really enjoyed their stay. They said everything was wonderful. It is a very charming and has wonderful history. They really thought the baby horses playing in the field across the street was an over the top touch.
…see more

Price per night from

$155

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$155

Distance approx 15.54 km from Canaan

(4) Excellent 

30

Gem of the Berkshires, walk to downtown & lake.

Berkshires / Great Barrington

Great Barrington house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 0.32 mi
  • Child Friendly
  • Air conditioning
“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are b
…see more

Price per night from

$299

Price per night from

$299

Distance approx 10.31 km from Canaan

(1) Excellent 

30

INTERIOR DESIGNERS BOTANICAL GARDENS

Berkshires / Lenox

Lenox cottage

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Nearest beach 3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$180

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$180

Distance approx 19.73 km from Canaan

(2) Excellent 

18

Mussmacher Porch

New York / Hudson

Hudson apartment

3 9 1 night min

  • 3 bedrooms
  • sleeps 9
  • 1 night min
  • Ski
  • Child Friendly

Price per night from

$125

Responds fast!
avg. 47 minutes

Price per night from

$125

Distance approx 14.44 km from Canaan

(14) Excellent 

Certificate of Excellence

55

RiverSong Suite In The Berkshires

Berkshires / North Egremont

North Egremont apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Air conditioning

Certificate of Excellence

Price per night from

$189

Responds fast!
avg. 35 minutes

Price per night from

$189

Distance approx 18.81 km from Canaan

16

Olde York Farm Distillery Suite

New York / Claverack

Claverack farmhouse

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$249

Price per night from

$249

Distance approx 12.64 km from Canaan

(2) Very Good 

12

Berkshires Spacious Comfortable Charming Farmhouse

Berkshires / Lee

Lee apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
…see more

Price per night from

$299

Price per night from

$299

Distance approx 16.56 km from Canaan

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

$249

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$249

Distance approx 12.08 km from Canaan

(1) Excellent 

13

The Gatehouse on Golden Hill

Berkshires / Lee

Lee house

4 14 3 nights min

  • 4 bedrooms
  • sleeps 14
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$796

Price per night from

$796

Distance approx 8.85 km from Canaan

(6) Excellent 

23

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

New York / Stephentown

Stephentown lodge

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$374

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$374

Distance approx 15.07 km from Canaan

(1) Excellent 

8

Writer's Room at Chestnut Lodge

Berkshires / Lee

Lee b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 8 mi
  • Ask about children
  • Air conditioning

Price per night from

$175

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$175

Distance approx 10.2 km from Canaan

22

Vacation Home on 10 Acres with Pool and Spa

Berkshires / Stockbridge

Stockbridge house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$747

Price per night from

$747

Distance approx 9.48 km from Canaan

(6) Excellent 

16

Family-friendly Cottage Near Lake, Tanglewood

Berkshires / Stockbridge

Stockbridge cottage

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$284

Responds fast!
avg. 3 hours 47 minutes

Price per night from

$284

Distance approx 18.23 km from Canaan

23

Bassinova-on-Hudson

New York / Coxsackie

Coxsackie villa

5 10 2 nights min

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

Price per night from

$2,490

Price per night from

$2,490

Distance approx 12.76 km from Canaan

13

Garfield House

Maine / Lee

Lee apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$175

Price per night from

$175

Distance approx 9.7 km from Canaan

4

Horse Room

Berkshires / Stockbridge

Stockbridge farmhouse

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$150

Price per night from

$150

Distance approx 12.76 km from Canaan

(1) Excellent 

10

Berkshire House Share-The Blue Room

Berkshires / Lee

Lee house

3 2 1 night min

  • 3 bedrooms
  • sleeps 2
  • 1 night min

Price per night from

$75

Price per night from

$75

Distance approx 14.15 km from Canaan

(1) Very Good 

14

Cozy and clean in Gt Barrington- available for October

Berkshires / Great Barrington

Great Barrington house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$150

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$150

Distance approx 15.59 km from Canaan

(1) Very Good 

4

Golden Triangle in the Berkshires

Berkshires / Hancock

Hancock house

2 4 2 nights min

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

Price per night from

$2,490

Price per night from

$2,490

Distance approx 9.79 km from Canaan

4

Iris Room

Berkshires / Stockbridge

Stockbridge farmhouse

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$150

Price per night from

$150

Distance approx 16.1 km from Canaan

21

Private Berkshire Estate w/Pool & Tennis Court

Berkshires / Great Barrington

Great Barrington house

4 12 min stay varies

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

Price per night from

$572

Price per night from

$572

Distance approx 7.72 km from Canaan

14

Modern Cozy Wooded Retreat

New York / Spencertown

Spencertown house

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$133

Price per night from

$133

Distance approx 11.31 km from Canaan

(1) Excellent 

20

Newly Renovated Colonial on the River! Sleeps 5-6

Berkshires / Stockbridge

Stockbridge house

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$284

Price per night from

$284