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

Spencertown Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Spencertown vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,172 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is AED 315
AED 434 total
includes taxes & fees
18 Oct - 19 Oct
Berkshire Mountain Lodge
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

2. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (180 reviews)
"Great little place."
United States
Kim
The price is AED 367
AED 411 total
includes taxes & fees
27 Oct - 28 Oct
Micosta Leisure Inn
A wooden deck with a staircase leading to a covered porch area.

3. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (63 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is AED 360
AED 486 total
includes taxes & fees
7 Oct - 8 Oct
All comforts of home
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is AED 331
AED 513 total
includes taxes & fees
11 Oct - 12 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is AED 257
AED 764 total
includes taxes & fees
5 Oct - 6 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A camping setup with a metal chair and a table by a river in a forest.

6. 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, (15 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 AED 735
AED 1,255 total
includes taxes & fees
5 Oct - 6 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AED 433
AED 568 total
includes taxes & fees
1 Nov - 2 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 AED 316
AED 831 total
includes taxes & fees
6 Oct - 7 Oct
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 AED 551
AED 699 total
includes taxes & fees
5 Oct - 6 Oct
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 AED 915
AED 1,164 total
includes taxes & fees
6 Oct - 7 Oct
Sugar Shack - 300 square feet of pure sweetness.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

11. 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, (7 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 AED 915
AED 1,164 total
includes taxes & fees
6 Oct - 7 Oct
BLUSH: Boutique TINY home*private spa*walk to town
A modern building with a wooden deck and a door.

12. 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 AED 804
AED 2,061 total
includes taxes & fees
5 Oct - 6 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden cabin with a porch, a grill, and a flower planter.

13. 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, (79 reviews)
"Excellent host!"
United States
Kenny
The price is AED 735
AED 1,395 total
includes taxes & fees
5 Oct - 6 Oct
Ideal location for summer and winter activities with plenty of outdoor space.
Dining

14. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 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 AED 744
AED 1,163 total
includes taxes & fees
6 Oct - 7 Oct
Leaf-Peeper Paradise in the Berkshires
A sandy beach with a lake and forest in the background.

15. 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, (5 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is AED 768
AED 1,206 total
includes taxes & fees
7 Oct - 8 Oct
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

16. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is AED 731
AED 1,399 total
includes taxes & fees
5 Oct - 6 Oct
Hudson NY’S Country Serenity Guest Suite.
A spacious room with a wooden ceiling, large windows, and a chandelier.

17. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is AED 1,561
AED 2,703 total
includes taxes & fees
5 Oct - 6 Oct
Luxury Barn Retreat — All-Season Escape Awaits!
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

18. 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)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AED 735
AED 1,280 total
includes taxes & fees
8 Oct - 9 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
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 AED 687
AED 1,341 total
includes taxes & fees
6 Oct - 7 Oct
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

20. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 779
AED 1,231 total
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Spencertown Hotel Reviews

Hotel On North

Hotel On North

8/10 Good
"Floors creak as it's an old hotel but the room and bathroom were really spacious. The town is meh bur the hotel was nice."
Robin 2-night trip
Posted 10 hours ago
Hotel On North

Frequently asked questions

Can I find a vacation rental in Spencertown?

Yes, you can find vacation rentals close to popular points of interest in Spencertown, or you can go with a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Spencertown has to offer?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental near 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 vacation rentals will I find in Spencertown?

Expedia has 3 vacation 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 larger area.

What’s a vacation rental in Spencertown like?

A vacation rental is a private property you can book for a couple of days or more in Spencertown. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.