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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Richmond holiday rentals

A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
Ellie’s Overlook, best view in the Berkshires!
A room with a large window, two sofas, and a small table.

2. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Exterior

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,260 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is £81
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
Indoor pool

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,837 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is £75
includes taxes & fees
9 Nov - 10 Nov
Vacation Village in the Berkshires
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
8.8 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 £149
includes taxes & fees
16 Nov - 17 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

6. 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 £163
includes taxes & fees
10 Nov - 11 Nov
1800s Carriage house in Berkshires / Hudson Valley
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

7. 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 £88
includes taxes & fees
14 Nov - 15 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

8. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Berkshires Apartment at the Stephentown Hotel
A white two-story house with a porch, surrounded by trees and a hill.

9. 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 £313
includes taxes & fees
17 Nov - 18 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

10. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is £465
includes taxes & fees
9 Nov - 10 Nov
Secluded Family Home in Serene Stockbridge Woods
A bedroom with a large bed, two bedside tables, a painting, and a clock on the wall.

11. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A modern kitchen with a dining area, built-in shelves, and a large window.

12. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is £222
includes taxes & fees
10 Nov - 11 Nov
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A cozy living room with a large window, wooden walls, and a television.

13. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

14. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A cozy living room with a fireplace, leather sofa, and a television.

15. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

16. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is £227
includes taxes & fees
10 Nov - 11 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

17. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

18. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (195 reviews)
"Great stay"
United States
George
The price is £83
includes taxes & fees
9 Nov - 10 Nov
Micosta Leisure Inn
A dining area with a wooden table, chairs, and a ceiling fan.

19. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
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 £226
includes taxes & fees
9 Nov - 10 Nov
Leaf-Peeper Paradise in the Berkshires
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

20. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox

10/10 Excellent

Helpful staff, clean room and great facilities.
United Kingdom
Laura
Reviewed July 30, 2026
Courtyard by Marriott Lenox Berkshires

Find out more about Richmond

Everything you need to know about Richmond holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Richmond holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Richmond holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Richmond holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Richmond. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Richmond holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Richmond holiday rentals we have selected for you start as low as £75 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Richmond rentals

At Expedia, we put the best Richmond holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Richmond rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Richmond holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Richmond. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Richmond?

Yes, there are holiday rentals close to the most popular sights in Richmond, or you can select a more secluded option if you're looking for a relaxing stay. Richmond is known for its wineries and mountain views. Make sure you have time to check out the restaurants while you're in the area.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Richmond is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Richmond?

With 21 Expedia holiday rentals, you're guaranteed to find just the right place for your Richmond stay.

What can I see and do in Richmond?

Lenox Mountain and Lenox Mountain Reserve are a couple of lovely local spots to get outside and enjoy nature. Furnace Brook Winery at Hilltop Orchards and Richmond Free Public Library are other places to visit while you're in town.

What are holiday rentals like in Richmond?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Richmond. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.

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