Photo by Chris Addams

Greenfield Holiday Rentals

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Holiday Rentals in Greenfield

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is AU$399
includes taxes & fees
24 Nov - 25 Nov
Cozy apartment located in quiet Williamsburg

Bear Creek Cabin

9.8 out of 10, Exceptional, (20)
"The home was beautiful and we enjoyed our stay! The only thing about the location, it’s very remote. We had an event in North Adams and had a nearly impossible time getting a ride share service or taxi to come pick us up. Other than that, a wonderful stay!"
The price is AU$935
includes taxes & fees
20 Dec - 21 Dec
Bear Creek Cabin

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

9.0 out of 10, Wonderful, (42)
"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

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!

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

10.0 out of 10, Exceptional, (39)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (129)
"The house was amazing, clean and comfortable. The area was great and very close to restaurants and shopping. I just can’t say enough good things about our experience. If I could give it more than five stars I would. "
Hadley Amherst Location.Explore the Valley Colleges!

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

9.6 out of 10, Exceptional, (40)
"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

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

9.8 out of 10, Exceptional, (95)
"This stay was wonderful. It's located about 4 miles from UMass, in a nice quiet area. We were greeted with farm fresh eggs, bakery cinnamon bread slices, local apples, homemade butter and organic milk in the fridge. The pictures are accurate and the place reminded me of an old farmhouse. There's a chicken coop right on the property. The beds were super comfortable and the hosts thought of everything. There were oatmeal packets, small candy bars, microwave popcorn, etc to snack on. There...
The price is AU$321
includes taxes & fees
24 Nov - 25 Nov
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Wilmington Vacation Rental Near Hiking and Skiing!

9.4 out of 10, Exceptional, (12)
"Beautiful cabin! Right in the middle of nature with plenty of things to do nearby. Host was exceptional!"
Wilmington Vacation Rental Near Hiking and Skiing!

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!"
comfort, luxury, privacy

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

9.6 out of 10, Exceptional, (125)
"We stayed two days but were mostly for sleep and sightseeing/visits. Certainly fit the bill for our needs. Would recommend to friends "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington

8.0 out of 10, Very good, (7)
"Great place, game room provided many laughs. It was clean, nice quite private property. We will stay again"
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (27)
"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "
Jacksonville Cabin w/ Wraparound Deck & Views

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

Cozy Cottage Along Idyllic Green River

10.0 out of 10, Exceptional, (43)
"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...
Cozy Cottage Along Idyllic Green River

Cozy Treetop Hideaway Near Harriman Reservoir!

9.2 out of 10, Wonderful, (12)
"Not as depicted You do not have access to the lake from The property The trees in the summer obscure the view of the lake Well equipped for bbq and games Dog friendly AC in the bedrooms would be ideal for sleeping as it was very humid this weekend"
Cozy Treetop Hideaway Near Harriman Reservoir!

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

10.0 out of 10, Exceptional, (39)
"We had a group of nine and had a great time. There are so many wonderful features including a fully stocked kitchen, activities for kids and an awesome outdoor area to hang out and relax. Would highly recommend this house. "
The price is AU$1,092
includes taxes & fees
16 Dec - 17 Dec
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (209)
"Clean and well supplied with fantastic views and close proximity to town.....a wonderful fall New England experience! "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

10.0 out of 10, Exceptional, (12)
"Love this property. We had everything we needed and then some. wasn't exactly sure as to where to put the trash as I don't have email on my phone , therefore I didn't receive the email about the trash and laundry until I got back home. I would rather have been able to text but everything worked out for us, and we had a wonderful, relaxing time."
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!

10.0 out of 10, Exceptional, (26)
"The house was perfect for a group of five of us. The kitchen and grill were great for our culinary needs. Thanks for letting us stay!"
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
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, (755)
"We had issues at checkin"
The price is AU$232
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Greenfield

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1003)
"When the heater came on it was pretty loud! Other than that everything was fine!"
The price is AU$174
includes taxes & fees
23 Dec - 24 Dec
Howard Johnson by Wyndham Amherst Hadley

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1008)
"George and Jamie were very nice and helpful "
The price is AU$161
includes taxes & fees
1 Dec - 2 Dec
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.
Beautiful view of the beach with palm trees

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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?

Cozy apartment located in quiet Williamsburg: This holiday home rental outside of Greenfield is in a rural location, and equipped with air conditioning and WiFi 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 Greenfield?

Connecticut River and Greenfield Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Old Greenfield Village and Poet's Seat Tower.

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.