A diner with a green roof and a red barn in the background.

Spencertown Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Spencertown holiday rentals

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

1. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (197 reviews)
"Great stay"
United States
George
The price is HK$647
HK$725 total
includes taxes & fees
19 Nov - 20 Nov
Micosta Leisure Inn
A large building with a prominent tower, surrounded by trees and a winding road.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,273 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is HK$602
HK$848 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

3. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is HK$600
HK$907 total
includes taxes & fees
21 Nov - 22 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A wooden deck with a staircase leading to a covered porch area.

4. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (65 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$770
HK$967 total
includes taxes & fees
16 Nov - 17 Nov
All comforts of home
A camping setup with a metal chair and a table by a river in a forest.

5. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (18 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is HK$1,569
HK$2,566 total
includes taxes & fees
22 Nov - 23 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

6. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is HK$549
HK$1,518 total
includes taxes & fees
16 Nov - 17 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A wooden deck with a staircase leading to a covered porch area.

7. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is HK$833
HK$1,039 total
includes taxes & fees
16 Nov - 17 Nov
All the comforts of home
A spacious living room with a dining area, a kitchen, and a large window.

8. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is HK$667
HK$1,662 total
includes taxes & fees
16 Nov - 17 Nov
1800s Carriage house in Berkshires / Hudson Valley
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

9. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,389
HK$1,678 total
includes taxes & fees
19 Nov - 20 Nov
The Brooks Motel: Exceptional Suite
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

10. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (4 reviews)
"This place was better than the photos. Everything was well planned out and extremely comfortable. The host was very attentive with great information about the area. Would definitely recommend."
United States
Lori S.
The price is HK$2,032
HK$2,478 total
includes taxes & fees
16 Nov - 17 Nov
Sugar Shack - 300 square feet of pure sweetness.
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

11. 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 HK$1,381
HK$2,392 total
includes taxes & fees
16 Nov - 17 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

12. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (8 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is HK$2,032
HK$2,478 total
includes taxes & fees
16 Nov - 17 Nov
BLUSH: Boutique TINY home*private spa*walk to town
A cozy living room with a sofa, a fireplace, and large windows.

13. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is HK$2,934
HK$4,912 total
includes taxes & fees
18 Nov - 19 Nov
Luxury Barn Near Hudson With New Private Sauna
A modern building with a wooden deck and a door.

14. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is HK$1,969
HK$4,508 total
includes taxes & fees
16 Nov - 17 Nov
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

15. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (80 reviews)
"We very much enjoyed our two week stay in July. The cabin suited our needs in every regard. Our lab was also able to fully relax, whether it was napping on the screen porch or sitting by the fire pit. For those looking to explore the region, the location could not be better situated. Hoping to return over Christmas."
United States
Richard M.
The price is HK$1,373
HK$2,698 total
includes taxes & fees
16 Nov - 17 Nov
Ideal location for summer and winter activities with plenty of outdoor space.
A dining area with a wooden table, chairs, and a ceiling fan.

16. A Cozy Berkshire Escape l Close to the Slopes

A Cozy Berkshire Escape l Close to the Slopes
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 HK$1,589
HK$2,353 total
includes taxes & fees
16 Nov - 17 Nov
A Cozy Berkshire Escape l Close to the Slopes
A cabin with a triangular window, wooden walls, and a bed with pillows.

17. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
The price is HK$2,169
HK$2,342 total
includes taxes & fees
11 Dec - 12 Dec
Gather Greene
A sandy beach with a lake and forest in the background.

18. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is HK$1,640
HK$2,550 total
includes taxes & fees
16 Nov - 17 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A backyard with a fire pit, wooden deck, and string lights.

19. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
The price is HK$1,467
HK$2,733 total
includes taxes & fees
16 Nov - 17 Nov
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

20. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.4 out of 10, Exceptional, (6 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is HK$1,561
HK$2,847 total
includes taxes & fees
16 Nov - 17 Nov
Hudson NY’S Country Serenity Guest Suite.
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 Spencertown Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Convenient location. 24 hour front desk"
David 1-night trip
Posted 3 hours ago
Quality Inn Great Barrington

Find out more about Spencertown

Search for holiday rentals in Spencertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Spencertown using one of the methods below:

  • View our selection of featured holiday rentals in Spencertown
  • Use the map to find apartments and other holiday homes in the Spencertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Spencertown while they last

Look no further and take a look at our great range of rental properties in Spencertown!

Frequently asked questions

Can I find a holiday rental in Spencertown?

Yes, there are holiday rentals close to the most popular sights in Spencertown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Spencertown has to offer?

Catskill Cottage Walk to Downtown & River Views: This holiday home rental outside of Spencertown offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Spencertown?

Expedia has 3 holiday rentals for your stay in Spencertown.

What’s there to see and do in Spencertown?

Explore the area and family-friendly sights such as Bousquet Ski Area, or get out into nature at a spot like Berkshire Botanical Garden. Norman Rockwell Museum and Catamount Aerial Adventure Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Spencertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Spencertown. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.