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Plainfield Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Plainfield holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,777 reviews)
"We had an amazing stay."
United States
Luke
The price is HK$630
HK$790 total
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,222 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is HK$673
HK$927 total
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

3. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is HK$2,119
HK$3,384 total
includes taxes & fees
25 Oct - 26 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A hot tub with a wooden deck and chairs, a white building with windows, and a clear sky.

4. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is HK$1,758
HK$3,909 total
includes taxes & fees
16 Nov - 17 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A log cabin with a balcony, surrounded by trees.

5. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,139
HK$4,698 total
includes taxes & fees
26 Oct - 27 Oct
Bear Creek Cabin
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

6. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is HK$2,549
HK$5,704 total
includes taxes & fees
25 Oct - 26 Oct
5BR Berkshire Home Mins To The Mountain
Interior

7. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The price is HK$2,835
HK$4,358 total
includes taxes & fees
8 Nov - 9 Nov
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

8. 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$1,165
HK$2,835 total
includes taxes & fees
26 Oct - 27 Oct
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

9. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
The price is HK$2,644
HK$10,378 total
includes taxes & fees
28 Oct - 29 Oct
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A living room with a beige sofa, a patterned rug, and a wooden floor.

10. Spacious & Cozy Ground Floor 2/3 Bed private suite

Spacious & Cozy Ground Floor 2/3 Bed private suite
Shelburne Falls
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful property with an exceptional host!"
United States
Russ D.
The price is HK$1,263
HK$2,831 total
includes taxes & fees
17 Nov - 18 Nov
Spacious & Cozy Ground Floor 2/3 Bed private suite
A modern two-story house with large windows and a balcony.

11. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (13 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is HK$3,923
HK$4,996 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Valley View Post & Beam Villa!
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

12. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (18 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is HK$1,138
HK$2,209 total
includes taxes & fees
28 Oct - 29 Oct
Penthouse Apartment on Park Street
A spacious kitchen with wooden flooring, a central island with stools, a dining table, and pendant lighting.

13. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (56 reviews)
"This home was comfy, really clean and hosts were easy to reach and chat with during our stay. My extended family had a great time getting together this summer staying at hosts’ home!"
United States
Griffin S.
The price is HK$2,294
HK$5,148 total
includes taxes & fees
25 Oct - 26 Oct
Spacious 5BR w/ Hot Tub & Games
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

14. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is HK$1,201
HK$1,963 total
includes taxes & fees
25 Oct - 26 Oct
Lovely 2nd Floor Apartment
A house with a staircase leading to a porch, surrounded by snow and string lights.

15. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (13 reviews)
"Nice place"
United States
Tom
The price is HK$1,589
HK$2,003 total
includes taxes & fees
26 Oct - 27 Oct
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

16. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
8.0 out of 10, Very good, (1 review)
"Very cute and welcoming B&B guest house. It was not clear to me that our private bathroom was across the hall. Some are and some not so check for that."
United States
Mikaela M.
The price is HK$812
HK$1,521 total
includes taxes & fees
25 Oct - 26 Oct
Rose room Victorian home queen bed private bath
A blue house with a porch, a wooden bench, and a door.

17. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is HK$509
HK$1,629 total
includes taxes & fees
3 Nov - 4 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

18. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is HK$2,188
HK$3,599 total
includes taxes & fees
17 Nov - 18 Nov
Greylock Cabin
A kitchen with white cabinets, a wooden dining table, and pendant lights.

19. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is HK$1,797
HK$3,778 total
includes taxes & fees
30 Oct - 31 Oct
A roomy remodeled retreat close to MassMoCA
A hallway with wooden flooring, white walls, and a bed in the background.

20. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is HK$1,579
HK$3,272 total
includes taxes & fees
26 Oct - 27 Oct
Shelburne Falls on Main
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 Plainfield Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"I loved this property. Nice room with fireplace and balcony, great shower, good breakfast, easy parking, and beautiful walking trail behind the hotel."
Barry 2-night trip
Posted less than an hour ago
The Yankee Inn

Find out more about Plainfield

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

  • View our selection of featured holiday rentals in Plainfield
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Look no further and take a look at our great range of rental properties in Plainfield!

Frequently asked questions

Can I find holiday rentals in Plainfield?

Yes, there are holiday rentals close to the most popular sights in Plainfield, or you can select a more secluded option if you're looking for a relaxing stay.

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

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Plainfield is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

What can I see and do in Plainfield?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Swift River. In the wider area, you’ll find Three Sisters Sanctuary and Berkshire East Ski Resort.

What are holiday rentals like in Plainfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Plainfield. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.