Photo by Chris Addams

Holiday Rentals in Greenfield

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Holiday Rentals in Greenfield

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (96)
"Easy check in, very clean and well stocked with everything needed. I was visiting my daughter at UMass who had to have knee surgery. There was lots of space for her to get around. It was also close to the University which was important for us as well."
The price is €206
includes taxes & fees
19 Jan - 20 Jan
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (22)
"great place to stay"
Charlemont Retreat on Chickley River w/ EV Charger

Wilmington Vacation Rental Near Hiking and Skiing!

9.0 out of 10, Wonderful, (16)
"We enjoyed our stay and all that the property had to offer. It is close by Mount Snow and all of the shops and restaurants. It was cozy and great to come back to at the end of a day of skiing. The house was stocked with supplies and all of the cabinets were nicely labeled as well."
Wilmington Vacation Rental Near Hiking and Skiing!

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.2 out of 10, Wonderful, (40)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (130)
"Wonderful, updated and well-stocked kitchen and IMMENSE refrigerator helped with making four mammoth feasts in a row for family, with grandkids and pooches underfoot. Terrific location, beautifully appointed house, and Colleen could not possibly be more responsive. Thanks for having us!!!"
Hadley Amherst Location.Explore the Valley Colleges!

Cozy 2-bedroom Unit with private backyard

10.0 out of 10, Exceptional, (21)
"Small but very clean and had everything we needed for our stay "
Cozy 2-bedroom Unit with private backyard

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

10.0 out of 10, Exceptional, (43)
"Very a accommodating "
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (41)
"My partner, my pet, and I spent Christmas week here and had a great time. The house is small but very cozy and well appointed and feels bigger than it is. The bed and couches are very comfortable, and the house gets plenty warm for cold winter weather. The location is a great starting point to explore Southern Vermont and Northern Massachusetts: whether you are skiing at Mount Snow, visiting Mass MOCA in North Adams, or getting dinner in Brattleboro or exploring any of the nearby villages,...
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

comfort, luxury, privacy

9.8 out of 10, Exceptional, (56)
"Great place to stay when visiting your student! Good for 1-3 people. Highly recommend!"
The price is €194
includes taxes & fees
10 Feb - 11 Feb
comfort, luxury, privacy

Bear Creek Cabin

9.8 out of 10, Exceptional, (24)
"Loved it, will definitely book again!"
The price is €592
includes taxes & fees
25 Jan - 26 Jan
Bear Creek Cabin

Outerwoods | stellar community amenities (pickleball) and skiing at Mt. Snow

9.8 out of 10, Exceptional, (9)
"We found the house to be spacious and cozy tucked away in the woods. Unfortunately the rain during the week we were there prevented us from doing everything we wanted to outdoors, like campfires. We appreciated finding a place that allowed us to bring our dog. Some updates could help improve this house such as a sliding glass door heading outside that is easier to open and close. The quiet atmosphere around the house was exactly what we were looking for with beautiful scenery. There were more...
Outerwoods | stellar community amenities (pickleball) and skiing at Mt. Snow

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (32)
"We had another great stay for us at the Fiddler's rest. The cabin is beautifully set in a private stetting in the forest. The interior design is colorful and tasteful. The cabin could comfortable host or group of 4 people. The internet connection was great. We would be happy to visit again!"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (28)
"Perfect cabin with beautiful views."
Jacksonville Cabin w/ Wraparound Deck & Views

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.4 out of 10, Exceptional, (6)
"Location is minutes away from town. Location was easy to find. House was very clean and had all that we needed. Perfect size for our group of 5 adults, each having our own bedroom. We found plenty to do in the area. Jane was very helpful giving us information of things to do, especially being a girl's weekend, she informed us of spas, shopping and great spots to see foliage, and nice restaurant nearby that had music. Would definitely stay here again."
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (76)
"Very cute and quiet location! Cabin has everything ine would need! Plenty of parking, and there are trails throughout the property. Its in the perfect spot, only 18 minutes from town. "
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (51)
"What a wonderful place to stay!! We were in town for my 50th high school reunion, hadn’t been back to the area in 35 years. Our accommodations enhanced a beautiful weekend, and the foliage was the cherry on top! Spacious, clean, tastefully furnished and decorated. Well equipped with every utensil, and kitchen appliance you could need! Comfy bed, great shower & good water pressure too! Secluded and quiet, but very convenient to Bernardston, Northfield and Greenfield as well as I-91. Highly...
Spectacular Mountain views with all the amentities nearby
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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Other types of properties in Greenfield you may be interested in

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (768)
"Staff was very friendly and accommodating. Despite some current renovation work, property was clean and quiet."
The price is €175
includes taxes & fees
9 Feb - 10 Feb
Hampton Inn & Suites Greenfield

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1000)
"Easiest check in ever!! Room was clean, adequate for our needs "
The price is €107
includes taxes & fees
3 Feb - 4 Feb
Howard Johnson by Wyndham Amherst Hadley

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1001)
"I I would happily stay there again. "
The price is €116
includes taxes & fees
26 Jan - 27 Jan
Colonial Motel And Spa
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.

Frequently asked questions

Are there holiday rentals in Greenfield?

Yes, there are holiday rentals close to the most popular sights in Greenfield, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Greenfield is known for its shops. Make sure you have time to check out the breweries and live music during your trip.

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

Kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley: This holiday home rental outside of Greenfield is located in the city centre, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Greenfield?

Choose from 3 Expedia holiday rentals in Greenfield for a memorable holiday.

What can I see and do in Greenfield?

Greenfield Beach and Connecticut River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Old Greenfield Village and Energy Park.

What are holiday rentals like in Greenfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenfield. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental 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 a popular choice for family trips or small group gatherings.