A waterfall cascading over rocks surrounded by autumn foliage.

Richmond Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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.
The price is HK$2,471
HK$5,422 total
includes taxes & fees
11 Nov - 12 Nov
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
The price is HK$7,045
HK$9,832 total
includes taxes & fees
29 Oct - 30 Oct
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, (1,238 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
The price is HK$673
HK$926 total
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,802 reviews)
"We had an amazing stay."
United States
Luke
The price is HK$630
HK$790 total
includes taxes & fees
1 Nov - 2 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
8.6 out of 10, Excellent, (7 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 HK$549
HK$1,614 total
includes taxes & fees
2 Nov - 3 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 HK$667
HK$1,767 total
includes taxes & fees
5 Nov - 6 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)
"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 HK$600
HK$977 total
includes taxes & fees
3 Nov - 4 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

8. 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 HK$756
HK$1,755 total
includes taxes & fees
29 Oct - 30 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

9. 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 HK$733
HK$1,827 total
includes taxes & fees
29 Oct - 30 Oct
Berkshires Apartment at the Stephentown Hotel
A white two-story house with a porch, surrounded by trees and a hill.

10. 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 HK$1,287
HK$3,382 total
includes taxes & fees
9 Nov - 10 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A lobby with leather sofas, a fireplace, and a stone wall.

11. 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 HK$879
HK$1,910 total
includes taxes & fees
1 Nov - 2 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

12. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (192 reviews)
"Great stay"
United States
George
The price is HK$774
HK$867 total
includes taxes & fees
1 Nov - 2 Nov
Micosta Leisure Inn
A Country Inn with a large, welcoming entrance and a parking area.

13. 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 HK$756
HK$1,755 total
includes taxes & fees
29 Oct - 30 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A room with a wooden floor, a desk with a chair, a lamp, a window with curtains, and a door.

14. 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 HK$2,676
HK$5,066 total
includes taxes & fees
2 Nov - 3 Nov
Secluded Family Home in Serene Stockbridge Woods
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

15. 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 HK$763
HK$1,772 total
includes taxes & fees
29 Oct - 30 Oct
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A dining area with a wooden table, chairs, and a ceiling fan.

16. 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 HK$1,589
HK$2,484 total
includes taxes & fees
3 Nov - 4 Nov
Leaf-Peeper Paradise in the Berkshires
A modern kitchen with a dining area, built-in shelves, and a large window.

17. 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 HK$1,765
HK$2,480 total
includes taxes & fees
1 Nov - 2 Nov
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

18. 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, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is HK$1,377
HK$3,089 total
includes taxes & fees
1 Nov - 2 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A residential garden with a stone border, various plants, and a house in the background.

19. 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, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is HK$1,679
HK$2,734 total
includes taxes & fees
17 Nov - 18 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Exterior

20. 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, (16 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 HK$1,569
HK$2,680 total
includes taxes & fees
29 Oct - 30 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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

The Yankee Inn

The Yankee Inn

8/10 Good
"We stayed at the Yankee Inn for 1 night. We had no problems with check-in. Our room was clean but outdated except the bathroom which was very nice. Good water pressure in the shower and the bed was comfortable. Unfortunately, due to myself not feeling well, we did not use the hot tub, enjoy the fire pit or try breakfast all of which would have likely improved our stay. Maybe next time!"
Jeanne 1-night trip
Posted 4 hours ago
The Yankee Inn

Find out more about Richmond

Search for holiday rentals in Richmond on Expedia! You can easily find your home rentals, villas, holiday apartments in Richmond using one of the methods below:

  • View our selection of featured holiday rentals in Richmond
  • Use the map to find apartments and other holiday homes in the Richmond neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Richmond while they last

Look no further and take a look at our great range of rental properties in Richmond!

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.