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98 Houses

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

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

Great rentals within 20 miles that match your search

Distance approx 18.96 km from Otis

(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 5.22 km from Otis Show on Map

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 16.66 km from Otis

(4) Excellent 

10

Comfortable Farmhouse in the Berkshires

Berkshires / West Stockbridge

West Stockbridge farmhouse

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$326

Price per night from

$326

Distance approx 18.84 km from Otis

(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

$187

Price per night from

$187

Distance approx 4.99 km from Otis Show on Map

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 19.53 km from Otis

(1) Excellent 

18

Hillhouse Log Cabin

New York / Hillsdale

Hillsdale log cabin

3 13 2 nights min

  • 3 bedrooms
  • sleeps 13
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfe
…see more

Price per night from

$426

Price per night from

$426

Distance approx 5.9 km from Otis Show on Map

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 14.78 km from Otis

(29) Excellent 

21

Gartner House, a charming home in Lenox

Berkshires / Lenox

Lenox apartment

4 7 2 nights min

  • 4 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Ask about pets
“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa,
…see more

Price per night from

$201

Price per night from

$201

Distance approx 12.37 km from Otis

(4) Excellent 

18

Lake House

Berkshires / Lee

Lee house

5 9 7 nights min

  • 5 bedrooms
  • sleeps 9
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$715

Price per night from

$715

Distance approx 15.65 km from Otis

(4) Very Good 

18

Lakefront Berkshires Ski/Summer House, Great Views

Berkshires / Great Barrington

Great Barrington house

4 10 min stay varies

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

Price per night from

$189

Price per night from

$189

Distance approx 10.15 km from Otis

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 14.84 km from Otis

24

NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

Berkshires / Lenox

Lenox house

3 6 3 nights min

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

Price per night from

$376

Responds fast!
avg. 10 minutes

Price per night from

$376

Distance approx 9.9 km from Otis

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 17.81 km from Otis

(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

$190

Responds fast!
avg. 35 minutes

Price per night from

$190

Distance approx 9.58 km from Otis

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 16.86 km from Otis

(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

$181

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$181

Distance approx 19.78 km from Otis

15

S. Berkshires Mountain Treehouse • Views • Privacy

Berkshires / Great Barrington

Great Barrington house

2 4 14 nights min

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

Price per night from

$187

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$187

Distance approx 9.33 km from Otis

7

the BIG room at chestnut lodge

Berkshires / Lee

Lee b and b

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$201

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$201

Distance approx 7.51 km from Otis Show on Map

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 14.32 km from Otis

(1) Excellent 

17

Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)

Berkshires / Stockbridge

Stockbridge cottage

2 4 2 nights min

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

Price per night from

$300

Responds fast!
avg. 13 minutes

Price per night from

$300

Distance approx 14.9 km from Otis

(2) Excellent 

10

Heart of Lenox

Berkshires / Lenox

Lenox house

2 4 2 nights min

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

Price per night from

$176

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$176

Distance approx 9.33 km from Otis

(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

$176

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$176

Distance approx 14.68 km from Otis

19

One of the Finest Homes and Best location in the Berkshires

Berkshires / Stockbridge

Stockbridge house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$701

Price per night from

$701

Distance approx 14.9 km from Otis

(2) Excellent 

30

Tranquil 3BR Stockbridge House w/Private Deck

Berkshires / Stockbridge

Stockbridge house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$216

Responds fast!
avg. 10 minutes

Price per night from

$216

Distance approx 13.44 km from Otis

24

Cozy Stockbridge Home - Walk To Golf Course!

Berkshires / Stockbridge

Stockbridge house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$211

Responds fast!
avg. 10 minutes

Price per night from

$211

Distance approx 14.97 km from Otis

23

Renovated 2 bedroom in Heart of Lenox

Berkshires / Lenox

Lenox apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$301

Price per night from

$301

Distance approx 9.33 km from Otis

(1) Excellent 

2

chestnut lodge Queens Room

Berkshires / Lee

Lee b and b

1 2 2 nights min

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

Price per night from

$146

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$146

Distance approx 14.76 km from Otis

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

$151

Price per night from

$151

Distance approx 17.95 km from Otis

(1) Excellent 

22

Berkshire Getaway at 'Tofu'S Retreat'

Berkshires / Alford

Alford chateau

3 6 7 nights min

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

Price per night from

$216

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$216

Distance approx 14.68 km from Otis

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

$151

Price per night from

$151

Distance approx 14.86 km from Otis

16

Beautifully Renovated Berkshires Farmhouse

Berkshires / West Stockbridge

West Stockbridge b and b

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$211

Price per night from

$211

Distance approx 10.45 km from Otis

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 16.38 km from Otis

14

Perfect for skiers in the Berkshires

Berkshires / Lee

Lee townhouse

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly

Price per night from

$118

Price per night from

$118

Distance approx 14.69 km from Otis

31

|The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

Berkshires / Stockbridge

Stockbridge house

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$451

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$451

Distance approx 14.74 km from Otis

(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

$286

Price per night from

$286

Distance approx 15.71 km from Otis

26

NEW! Lakefront Berkshires House w/Deck, Dock +Boat

Berkshires / Housatonic

Housatonic house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$180

Responds fast!
avg. 10 minutes

Price per night from

$180