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Our top choices for Richmond holiday homes
1. 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 NZ$378
includes taxes & fees
7 Dec - 8 Dec
2. 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 NZ$382
includes taxes & fees
10 Nov - 11 Nov
3. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
Christine C.
The price is NZ$723
includes taxes & fees
10 Nov - 11 Nov
4. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
Ofer C.
The price is NZ$1,165
includes taxes & fees
16 Nov - 17 Nov
5. 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 NZ$538
includes taxes & fees
17 Nov - 18 Nov
6. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat 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 NZ$539
includes taxes & fees
10 Nov - 11 Nov
7. 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 NZ$590
includes taxes & fees
10 Nov - 11 Nov
8. 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."
Patricia O.
The price is NZ$1,083
includes taxes & fees
10 Nov - 11 Nov
9. 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.
10. 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 :)"
Anonymous traveller
The price is NZ$1,463
includes taxes & fees
1 Dec - 2 Dec
11. 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.
12. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
William C B.
The price is NZ$510
includes taxes & fees
12 Nov - 13 Nov
13. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ DeckStephentown
9.2 out of 10, Wonderful, (10 reviews)
"Great property and the host was extremely responsive and helpful."
Robbie S.
The price is NZ$999
includes taxes & fees
10 Nov - 11 Nov
14. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
Janet G.
The price is NZ$576
includes taxes & fees
10 Nov - 11 Nov
15. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is NZ$2,250
includes taxes & fees
7 Dec - 8 Dec
16. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
Frank M.
The price is NZ$661
includes taxes & fees
10 Nov - 11 Nov
17. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!Pittsfield
8.6 out of 10, Excellent, (11 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
Stephen L.
The price is NZ$834
includes taxes & fees
10 Nov - 11 Nov
18. 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)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
Brian C.
The price is NZ$640
includes taxes & fees
10 Nov - 11 Nov
19. 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 NZ$239
includes taxes & fees
10 Nov - 11 Nov
20. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
Amit
The price is NZ$926
includes taxes & fees
10 Nov - 11 Nov
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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Get away to relaxing Richmond! Enjoy the horse riding, wineries and local cuisine.
