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Holiday Homes in Richmond

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Richmond holiday homes

A bedroom with a bed, bedside lamp, and a window with curtains.

1. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is NZ$1,206
includes taxes & fees
29 Sept - 30 Sept
Ellie’s Overlook, best view in the Berkshires!
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

2. 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 NZ$362
includes taxes & fees
27 Sept - 28 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

3. 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 NZ$407
includes taxes & fees
28 Sept - 29 Sept
1800s Carriage house in Berkshires / Hudson Valley
A white two-story house with a porch, surrounded by trees and a hill.

4. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
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. "
United States
Christine C.
The price is NZ$801
includes taxes & fees
5 Oct - 6 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

5. Riverside Retreat in the Berkshires

Riverside Retreat 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 NZ$551
includes taxes & fees
28 Sept - 29 Sept
Riverside Retreat in the Berkshires
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is NZ$966
includes taxes & fees
25 Oct - 26 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

7. 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 NZ$606
includes taxes & fees
11 Oct - 12 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A camping setup with a metal chair and a table by a river in a forest.

8. 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 NZ$586
includes taxes & fees
27 Sept - 28 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

9. 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 NZ$588
includes taxes & fees
25 Oct - 26 Oct
Home in Great Barrington
A spacious room with a wooden ceiling, large windows, and a chandelier.

10. 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 NZ$1,270
includes taxes & fees
28 Sept - 29 Sept
Luxury Barn Retreat — All-Season Escape Awaits!
A modern building with a wooden deck and a door.

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!"
United States
Terri E.
The price is NZ$1,010
includes taxes & fees
28 Sept - 29 Sept
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

12. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is NZ$954
includes taxes & fees
29 Sept - 30 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"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 NZ$502
includes taxes & fees
27 Sept - 28 Sept
Real Estate: Therapy - Lake, Laundry, Love it
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

14. 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, (40 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 NZ$1,475
includes taxes & fees
28 Sept - 29 Sept
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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.

15. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$645
includes taxes & fees
28 Sept - 29 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A two-story house with a front porch, surrounded by lush greenery and trees.

16. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
The price is NZ$941
includes taxes & fees
27 Sept - 28 Sept
Perfect House In Hillsdale, Brings Friends & Fam
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$689
includes taxes & fees
29 Sept - 30 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

18. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is NZ$1,510
includes taxes & fees
18 Oct - 19 Oct
Stylish Mid-century Modern Berkshires Cape
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

19. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is NZ$1,024
includes taxes & fees
28 Sept - 29 Sept
Treetop Hideaway in Tyringham
A wooden deck with a table and chairs, surrounded by a white railing.

20. 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
8.4 out of 10, Very good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is NZ$923
includes taxes & fees
13 Oct - 14 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 Richmond Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Great location to Tanglewood, 11 min ride. Clean room, comfy beds, great shower. Loved the pool and hot tub. Breakfast was just okay. We went down 20 minutes before breakfast was to be closed and not much there to be had. I had to ask for a bagel and no waffles."
Wendy 1-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Richmond

Richmond Holiday Homes information

Number of reviews
197
Accommodation
405 Holiday Homes
Lowest Price
NZ$362
Highest Price
NZ$1,510