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Compare 150 Vacation Homes in Greenfield with updated reviews, rates, and availability.

Charlemont Vacation Rental | 4BR | 2BA | 3,000 Sq Ft | Stairs Required

"Our family had a wonderful stay. The house was very comfortable and the owner was very responsive. The sound of the river right outside was delightful! The bathrooms are very nicely updated - a nice perk when staying in an older home. "

Best night's sleep on king size sleigh bed

"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."

AED 759 total

includes taxes & fees

12 Jan - 13 Jan

The Valley is known for our picturesque red tobacco barns and expansive cornfields.

"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. "

"Great house and property. Best great room around! Location is perfect. The owner is very friendly and knowledgeable about the house and location."

"Very nice place, clean, great communication. "

"Mid century Mod funtional house. Looks exactly as pictures. Attentive Host. Comfortable beds and furnishings. Secluded location .Must have 4x4 to get up driveway in winter!!! Yes would highly recommend and hope to be back soon!"

AED 2,984 total

includes taxes & fees

12 Jan - 13 Jan

"Great location near restaurants and stores. House is "

AED 1,668 total

includes taxes & fees

7 Feb - 8 Feb

Bike ride on the Norwottuck Rail Trail( entrance to trail 2-minutes from the house) to the CT River- Bring your bikes and enjoy!

"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. "

The house was originally built in 1864 and completely updated in 2009

"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!"

Green River Cottage. Walk up ramp to enter patio area, lockbox on inside door.

"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...

"We stayed for Thanksgiving week. The house was more than big enough for our group of nine. The open kitchen/living room/dining room worked great for preparing and eating Thanksgiving dinner together. My wife identified an issue with the outdoor gas grill; the hosts had the grill replaced quickly and we were able to use it as planned. The hosts were very responsive and helpful. We would definitely stay here again."

Wilmington Vacation Rental | 4BR | 2BA | 1,336 Sq Ft | Stairs Required

"Everything was as-advertised! Very happy with our stay!"

Welcome to our Whitingham Wonderland. Enjoy gas fireplace, smart tv, cozy throws

"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!"

"My boyfriend and I (and our dog) really enjoyed this place. It’s on a quiet road, tucked up into a woodsy hill which gives the feeling of being secluded, while in actuality not being far from a main road. The listing is pretty accurate; the house is absolutely covered in windows, which allows for plenty of fresh air and natural light. The master bed is super comfortable, and the master bathroom is really nice too. I was a little apprehensive about the lack of air conditioning, but there is a...

"Very nice and cosy house for a weekend gateway. House is spacious with everything you need for a weekend. The outside hot-tub brings something magical to the stay. 100% recommand!"

"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."

Welcome! Plenty of space to yourselves to relax and soak in great outdoors!

"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. "

"We stayed at the Mountain View for a work field trip. We were celebrating the delivery of several pianos we rebuilt for the Yellow Barn I'm Putney. We spent most of our time outside, but when we came back, it was delightful. This is a beautiful property, very clean, and very cozy"