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Richmond Holiday Rentals

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Holiday Rentals in Richmond

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2126)
"Clean and great pool and hot tub facilities "
United States
Alyce
The price is NZ$202
includes taxes & fees
12 Nov - 13 Nov
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
The price is NZ$296
includes taxes & fees
10 Nov - 11 Nov
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (130)
"It's a beautiful little place with a wonderful owner. Rooms are clean and a good price"
United States
Gail
The price is NZ$235
includes taxes & fees
21 Nov - 22 Nov
Micosta Leisure Inn

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
The price is NZ$326
includes taxes & fees
10 Nov - 11 Nov
Taborton Harvest Boulder Pines Cabin in the woods

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
8.8 out of 10, Excellent, (3)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$529
includes taxes & fees
10 Nov - 11 Nov
Pet Friendly Riverfront Home in Great Barrington

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
The price is NZ$1,976
includes taxes & fees
18 Nov - 19 Nov
Hancock Village Inn Near Jiminy Peak

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
The price is NZ$569
includes taxes & fees
10 Nov - 11 Nov
Charming 3-bedroom Cabin for nature lovers

Peace and quiet on the lake

Sherwood Forest
9.6 out of 10, Exceptional, (227)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is NZ$1,419
includes taxes & fees
16 Nov - 17 Nov
Spacious 5-bedroom house in charming Lee with WiFi

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham
9.6 out of 10, Exceptional, (93)
"The house was very clean and well stocked. There were so many fun things to do - swimming pool, ping pong, darts, air hockey, gym, pinball, basketball hoop, foosball, etc. it was a great house for 4 families. The owner was very communicative and responded quickly to questions about the neighborhood, it was also very well located. Highly recommend!"
United States
Daisy H.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (132)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
8.8 out of 10, Excellent, (6)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
The price is NZ$961
includes taxes & fees
10 Nov - 11 Nov
Comfortable Berkshires retreat on mtn resort, SISO

The Lakeshore House

Niverville
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
The price is NZ$1,426
includes taxes & fees
10 Nov - 11 Nov
The Lakeshore House

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (149)
"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."
United States
Wendy Cameron L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Taborton Harvest Timber Trails Unique cabin experience

Sand Lake
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is NZ$326
includes taxes & fees
11 Nov - 12 Nov
Taborton Harvest Timber Trails Unique cabin experience
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

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, 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 NZ$202 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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: This holiday home rental outside of Richmond offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a fridge, a stovetop and a coffee maker, so that you can cook with friends or family. You can relax into your holiday with a garden and table football.

How many holiday rentals are there in Richmond?

With 19 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 Reserve and Lenox Mountain are a couple of lovely local spots to get outside and enjoy nature. Furnace Brook Winery at Hilltop Orchards and Pleasant Valley Wilderness Sanctuary 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.