Plainfield Vacation Rentals

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Check prices for these dates

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

Our top choices for Plainfield vacation rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,257 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is CA $107
CA $151 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
Indoor pool

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,830 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is CA $112
CA $141 total
includes taxes & fees
Nov 24 - Nov 25
Vacation Village in the Berkshires
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

3. 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 CA $157
CA $421 total
includes taxes & fees
Nov 10 - Nov 11
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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 CA $230
CA $566 total
includes taxes & fees
Nov 10 - Nov 11
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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.

5. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 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 CA $203
CA $373 total
includes taxes & fees
Nov 8 - Nov 9
Penthouse Apartment on Park Street
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

6. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is CA $214
CA $332 total
includes taxes & fees
Nov 9 - Nov 10
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

7. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is CA $129
CA $240 total
includes taxes & fees
Nov 9 - Nov 10
2 Twin beds on 1st floor with En-suite bathroom.
A blue house with a porch, a wooden bench, and a door.

8. 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 CA $122
CA $317 total
includes taxes & fees
Nov 9 - Nov 10
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

9. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $161
CA $276 total
includes taxes & fees
Nov 9 - Nov 10
Private room with En-suite bathroom Marigold Room
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 CA $225
CA $485 total
includes taxes & fees
Nov 9 - Nov 10
Spacious & Cozy Ground Floor 2/3 Bed private suite
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

11. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is CA $205
CA $376 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A hallway with wooden flooring, white walls, and a bed in the background.

12. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
10.0 out of 10, Exceptional, (1 review)
"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 CA $281
CA $553 total
includes taxes & fees
Nov 9 - Nov 10
Shelburne Falls on Main
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

13. 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 CA $345
CA $556 total
includes taxes & fees
Dec 6 - Dec 7
Charming, updated 3 bedroom farmhouse farm stay.
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 CA $135
CA $295 total
includes taxes & fees
Nov 8 - Nov 9
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

15. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
The price is CA $154
CA $388 total
includes taxes & fees
Nov 9 - Nov 10
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

16. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
The price is CA $225
CA $427 total
includes taxes & fees
Nov 8 - Nov 9
Downtown | Waterfront | Walk to Shops
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

17. 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 CA $145
CA $257 total
includes taxes & fees
Nov 9 - Nov 10
Rose room Victorian home queen bed private bath
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

18. 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 CA $135
CA $295 total
includes taxes & fees
Nov 8 - Nov 9
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
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.

19. 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, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is CA $204
CA $502 total
includes taxes & fees
Nov 9 - Nov 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A house with a staircase leading to a porch, surrounded by snow and string lights.

20. 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 CA $160
CA $198 total
includes taxes & fees
Nov 8 - Nov 9
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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

A two-story house with a porch, a balcony, and a chimney.
Blooming Inn

Blooming Inn

Blooming Inn
Shelburne Falls

10/10 Excellent

Amazing location lots of space to loung around and owners are very nice
Canada
Nathalie
Reviewed July 19, 2025
Blooming Inn

Find out more about Plainfield

Everything you need to know about Plainfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Plainfield vacation rental for you. At Expedia, you can take your pick from private vacation 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 Plainfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Plainfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Plainfield. 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 Plainfield vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Plainfield vacation rentals we have selected for you start as low as CA $107 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Plainfield rentals

At Expedia, we put the best Plainfield vacation 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 Plainfield 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 Plainfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Plainfield. 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 vacation rentals in Plainfield?

Yes, we have vacation rentals close to top points of interest in Plainfield, or you can choose a more secluded option if you're looking for relaxation.

What's the top vacation rental that Plainfield has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation 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 larger area, you’ll find Three Sisters Sanctuary and Berkshire East Ski Resort.

What are vacation rentals like in Plainfield?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Plainfield. Vacation rentals offer extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family gatherings.