Photo by Charlie Rhodes
Spencertown Vacation Rentals
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Our top choices for Spencertown vacation rentals
1. Micosta Leisure Inn
Micosta Leisure InnHudson
9.2 out of 10, Wonderful, (197 reviews)
"Great stay"
George
The price is CA $118
CA $132 total
includes taxes & fees
Nov 19 - Nov 20
2. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,273 reviews)
"Excellent stay!!!!"
Susan J
The price is CA $110
CA $154 total
includes taxes & fees
Dec 6 - Dec 7
3. Cozy 1-bedroom studio in serene Great Barrington with AC
Cozy 1-bedroom studio in serene Great Barrington with ACGreat Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
bob i.
The price is CA $109
CA $165 total
includes taxes & fees
Nov 22 - Nov 23
4. All comforts of home
All comforts of homeHudson
9.6 out of 10, Exceptional, (65 reviews)
"Loved the place and would love to come back. "
Georgine
The price is CA $140
CA $176 total
includes taxes & fees
Nov 16 - Nov 17
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!"
Jess S.
The price is CA $285
CA $470 total
includes taxes & fees
Nov 22 - Nov 23
6. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew 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. "
Joanna P.
The price is CA $100
CA $278 total
includes taxes & fees
Nov 16 - Nov 17
7. All the comforts of home
All the comforts of homeHudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
Julie B.
The price is CA $152
CA $189 total
includes taxes & fees
Nov 16 - Nov 17
8. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew 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)"
Leslie H.
The price is CA $121
CA $301 total
includes taxes & fees
Nov 16 - Nov 17
9. The Brooks Motel: Exceptional Suite
The Brooks Motel: Exceptional SuiteHillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
Joan
The price is CA $253
CA $302 total
includes taxes & fees
Nov 16 - Nov 17
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."
Lori S.
The price is CA $370
CA $454 total
includes taxes & fees
Nov 16 - Nov 17
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."
Eric H.
The price is CA $251
CA $435 total
includes taxes & fees
Nov 16 - Nov 17
12. BLUSH: Boutique TINY home*private spa*walk to town
BLUSH: Boutique TINY home*private spa*walk to townChatham
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!"
scott B.
The price is CA $370
CA $454 total
includes taxes & fees
Nov 16 - Nov 17
13. Luxury Barn Near Hudson With New Private Sauna
Luxury Barn Near Hudson With New Private SaunaEast Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
Michael T.
The price is CA $534
CA $919 total
includes taxes & fees
Nov 18 - Nov 19
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!"
Terri E.
The price is CA $358
CA $826 total
includes taxes & fees
Nov 16 - Nov 17
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."
Richard M.
The price is CA $250
CA $495 total
includes taxes & fees
Nov 16 - Nov 17
16. A Cozy Berkshire Escape l Close to the Slopes
A Cozy Berkshire Escape l Close to the SlopesGreat 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."
Kelly B.
The price is CA $289
CA $430 total
includes taxes & fees
Nov 16 - Nov 17
17. Gather Greene
Gather GreeneCoxsackie
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."
Jabari
The price is CA $391
CA $422 total
includes taxes & fees
Dec 11 - Dec 12
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, LakeGreat 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!"
Kristin O.
The price is CA $268
CA $429 total
includes taxes & fees
Nov 16 - Nov 17
19. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NYStottville
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!"
Ross O.
The price is CA $267
CA $499 total
includes taxes & fees
Nov 16 - Nov 17
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."
David P.
The price is CA $284
CA $519 total
includes taxes & fees
Nov 16 - Nov 17
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
8/10 Good
Find out more about Spencertown
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Spencertown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
