Plainfield Holiday Rentals

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Holiday Rentals in Plainfield

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (858)
"Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it"
The price is NZ$278
per night
2 Jun - 3 Jun
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (34)
"Nice place!"
The price is NZ$414
per night
4 Jun - 5 Jun
Cozy apartment located in quiet Williamsburg
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Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (117)
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Bear Creek Cabin
10.0 out of 10, Exceptional, (14)
"Very well thought out rental home. Everything you could possibly need for cooking and all thought out to reduce your time cleaning and more time on the river. No issues and we had a great time. Thanks again,"
The price is NZ$982
per night
3 Jun - 4 Jun
Bear Creek Cabin
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (205)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (15)
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (91)
"Wonderful property for family and dog!"
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (66)
"I absolutely loved this property! It was immaculate and had everything someone would need. The bed was very comfortable as was the living room furniture. I loved sitting out on the deck at night and watching the deer. The fire pit and the hot tub are a bonus. I enjoyed my stay and can’t wait to return."
Hearts Desire is a furnished whole house in a small, colorful garden center.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (35)
"Amazing House, so much character. More than enough room for large family meals and gatherings. My family really enjoyed it. Having no snow was a disappointment, but we will try again another year. Thank you"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
"I adored my stay at The Stone School. Rich and Cheryl were terrific hosts who had great suggestions for food and things to do. And the whole experience was easy to navigate. Excellent marks for cleanliness, comfort, ease of parking, quiet & solitude, quaintness, local pleasures. I found it perfect for myself and it would also be ideal for a couple (or perhaps a couple with one or two young children.) The bathroom is on the first floor with a modern sink and vanity; everything looks brand...
Charming historic cottage on scenic road to Mt. Greylock
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Amherst, Perfect Location, UMass, Smith, MHC!
10.0 out of 10, Exceptional, (11)
"We had the most perfect stay during our home renovation. We needed a place last minute, and we couldnt have found a more perfect house. The backyard was perfect for play and the house was super comfortable. We stayed for a week and we loved how easy it was to get to Whole Foods, Target, and Trader Joe’s. As a local, if we ever have friends in the area visiting, I would definitely recommend this VRBO."
Amherst, Perfect Location, UMass, Smith, MHC!
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See all available properties in Plainfield
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.

Other types of properties in Plainfield you may be interested in

Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (249)
"I liked this Property very much. The Staff was fantastic. Beautiful Hotel. Unfortunately, will probably not come back. They do not accept American Dollars. I reminded them that they are in the United States. I will not support any Corporation that does not accept Dollars. So, If you have a bad credit score, because of a Divorce, or misfortune, and do not have a credit card, you are not welcome. Sorry, that is discrimination. No one should be excluded, especially if they have...
The price is NZ$180
per night
30 May - 31 May
Life House Berkshires
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (924)
"A great place to stay in North Adams. Clean, friendly and located just a couple of miles from an outstanding breakfast restaurant. "
The price is NZ$260
per night
12 Jun - 13 Jun
Hotel Downstreet
Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
7.4 out of 10, Good, (1000)
"Staff was great. Room pretty clean, but cracked window, pool out of service but the front outside had beautiful landscaping and picnic table. 0 frills, yet location was perfect for our stay."
The price is NZ$200
per night
30 May - 31 May
Red Roof Inn PLUS+ South Deerfield – Amherst
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Plainfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Plainfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Plainfield. Seeing all the best attractions is bound to make you fall in love with Plainfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Plainfield short-term rentals, that won’t be hard to do.

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?

Cozy apartment located in quiet Williamsburg: This holiday home rental outside of Plainfield is in a rural location, and equipped with air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Berkshire East Ski Resort and Zoar Outdoor/Deerfield Valley Canopy Tours.

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.

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