A forest with a winding road and a mountain in the background.

Holiday Homes in Otis

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Otis holiday homes

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

1. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AU$396
includes taxes & fees
4 Nov - 5 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

2. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$499
includes taxes & fees
5 Nov - 6 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

3. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$524
includes taxes & fees
5 Nov - 6 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

4. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$750
includes taxes & fees
16 Nov - 17 Nov
Treetop Hideaway in Tyringham
A house with a porch, a garden with pink flowers, and a stone wall along the road.

5. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (154 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is AU$488
includes taxes & fees
3 Nov - 4 Nov
Big farmhouse in the foothills of the Berkshires
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

6. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AU$452
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
An outdoor patio with a stone table and chairs, a grill, and a stone fireplace.

7. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is AU$1,781
includes taxes & fees
2 Nov - 3 Nov
Maya's Garden House
A dining area with a wooden table, chairs, and a ceiling fan.

8. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AU$421
includes taxes & fees
2 Nov - 3 Nov
Leaf-Peeper Paradise in the Berkshires
A modern living room with a sofa, armchair, coffee table, and TV.

9. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is AU$856
includes taxes & fees
2 Dec - 3 Dec
Spacious Central Berkshires Home for Groups
521_Great Barrington_19

10. Maya's Garden House: Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

Maya's Garden House: Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Great Barrington
The price is AU$1,875
includes taxes & fees
2 Nov - 3 Nov
Maya's Garden House: Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
A living room with a sofa, armchairs, a coffee table, and a television.

11. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

12. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is AU$465
includes taxes & fees
2 Nov - 3 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

13. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is AU$1,122
includes taxes & fees
23 Nov - 24 Nov
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

14. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is AU$873
includes taxes & fees
2 Nov - 3 Nov
Secluded Family Home in Serene Stockbridge Woods
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

15. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AU$933
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A wooden cabin interior with a bench, a rug, and a hanging plant.

16. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is AU$270
includes taxes & fees
8 Nov - 9 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

17. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$570
includes taxes & fees
4 Nov - 5 Nov
Cheerful 3-bedroom cottage with woodstove
A wooden interior with a sectional sofa, a coffee table, and large windows offering a forest view.

18. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is AU$1,822
includes taxes & fees
30 Nov - 1 Dec
Beautiful and Private Home Centrally Located in the Berkshires
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

19. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AU$1,731
includes taxes & fees
4 Nov - 5 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A cozy room with two beds, large windows, and a view of a snowy landscape.

20. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is AU$377
includes taxes & fees
3 Nov - 4 Nov
The Creation Station is a cozy place so make yourself at home.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Otis Hotel Reviews

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Great experience!"
Sunny 3-night trip
Posted 17 hours ago
Prospect Berkshires

Find out more about Otis

Otis Holiday Homes information

Number of reviews
459
Accommodation
354 Holiday Homes
Lowest Price
AU$270
Highest Price
AU$1,731

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