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99 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

$687

Price per night from

$687

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

$115

Responds fast!
avg. 15 minutes

Price per night from

$115

Great rentals within 20 miles that match your search

Distance approx 10.91 km from Otis

24

3BR Lee House w/ Easy Access to Main Street!

Berkshires / Lee

Lee house

1 10 min stay varies

  • 1 bedroom
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$240

Responds fast!
avg. 10 minutes

Price per night from

$240

Distance approx 15.22 km from Otis

5

Cozy Modern Condo for the Berkshires

Berkshires / West Stockbridge

West Stockbridge condo

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$250

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$250

Distance approx 9.77 km from Otis

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. 10 minutes

Price per night from

$110

Distance approx 5.26 km from Otis Show on Map

(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

$275

Price per night from

$275

Distance approx 3.91 km from Otis Show on Map

(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

$149

Price per night from

$149

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

$185

Price per night from

$185

Distance approx 15.32 km from Otis

(2) Excellent 

8

Cozy & Modern Home -mins from Tanglewood & Kripalu

Berkshires / West Stockbridge

West Stockbridge apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$100

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$100

Distance approx 13.84 km from Otis

13

Designer Loft Style Residence

Berkshires / Sheffield

Sheffield house

3 6 7 nights min

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

Price per night from

$450

Price per night from

$450

Distance approx 5.18 km from Otis Show on Map

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

$427

Responds fast!
avg. 3 hours 33 minutes

Price per night from

$427

Distance approx 19.69 km from Otis

(1) Excellent 

20

Renovated Barn

Connecticut / Taconic

Taconic house

3 6 2 nights min

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

Price per night from

$350

Responds fast!
avg. 32 minutes

Price per night from

$350

Distance approx 17.11 km from Otis

(1) Excellent 

24

'Butterfly Hill' West Stockbridge Home on 3 Acres!

Berkshires / West Stockbridge

West Stockbridge house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$165

Price per night from

$165

Distance approx 17.65 km from Otis

(7) Excellent 

18

Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.

Berkshires / West Stockbridge

West Stockbridge house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly
“A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits
…see more

Price per night from

$275

Price per night from

$275

Distance approx 15.11 km from Otis

6

Stunning Home! 120 Acres! Amazing!

Berkshires / Great Barrington

Great Barrington house

9 16 3 nights min

  • 9 bedrooms
  • sleeps 16
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$3,600

Price per night from

$3,600

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

$400

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$400

Distance approx 10.69 km from Otis

12

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Berkshires / Lee

Lee apartment

2 6 2 nights min

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

Price per night from

$375

Price per night from

$375

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

$179

Price per night from

$179

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

$189

Responds fast!
avg. 35 minutes

Price per night from

$189

Distance approx 13.94 km from Otis

(2) Very Good 

12

Heart of the Berkshires!

Berkshires / Lenox

Lenox house

3 6 2 nights min

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

Price per night from

$225

Price per night from

$225

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

$175

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$175

Distance approx 16.86 km from Otis

(1) Excellent 

34

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

$105

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$105

Distance approx 16.22 km from Otis

(36) Excellent 

20

Berkshire Farmhouse Vacation

Berkshires / West Stockbridge

West Stockbridge house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden
“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l
…see more

Price per night from

$260

Price per night from

$260

Distance approx 11.75 km from Otis

(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

$300

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$300

Distance approx 12.38 km from Otis

26

3BD Newly Rennovated Contempoary Near Stockbridge

Berkshires / Stockbridge

Stockbridge house

3 6 min stay varies

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

Price per night from

$300

Price per night from

$300

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

$200

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$200

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

$175

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$175

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

$186

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$186

Distance approx 14.55 km from Otis

(1) Excellent 

24

Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu

Berkshires / Stockbridge

Stockbridge cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$299

Responds fast!
avg. 13 minutes

Price per night from

$299

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

$700

Price per night from

$700

Distance approx 11.39 km from Otis

15

House share/room for rent

Berkshires / Lee

Lee room

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi

Price per night from

$67

Price per night from

$67

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

$215

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$215

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

$150

Price per night from

$150

Distance approx 14.6 km from Otis

24

NEW! House w/ Kayak - Walk to Stockbridge Bowl!

Berkshires / Lenox

Lenox house

3 6 min stay varies

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

Price per night from

$185

Price per night from

$185

Distance approx 15.33 km from Otis

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

$575

Price per night from

$575

Distance approx 14.94 km from Otis

24

NEW-Norfolk Countryside Home 30 Min to Ski Sundown

Connecticut / Norfolk

Norfolk house

4 5 min stay varies

  • 4 bedrooms
  • sleeps 5
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$215

Price per night from

$215

Distance approx 4.76 km from Otis Show on Map

(13) 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 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

$285

Price per night from

$285