A snow-covered town with a prominent church steeple, red brick buildings, and a clear blue sky.

Greenfield Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Greenfield vacation rentals

Exterior detail

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
9.6 out of 10, Exceptional, (8 reviews)
"We had a great"
United States
Meredith B.
$248 nightly
The price is $277
Jul 6 - Jul 7
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (58 reviews)
"Very clean and cozy apartment. "
United States
Kim G.
$180 nightly
The price is $201
Jun 30 - Jul 1
Total with taxes and fees
Lovely 2nd Floor Apartment
Exterior

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, (6 reviews)
"Nice place"
United States
Tom
$229 nightly
The price is $255
Jul 15 - Jul 16
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
$129 nightly
The price is $136
Jun 30 - Jul 1
Total with taxes and fees
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (5 reviews)
"This place can only be described with one word, "WOW". That is the exact thing I said when pulling up to it. The driveway is steep and dirt so it can be intimidating but it isn't that bad at all. We went here on our honeymoon and had to ride 3 hours to get there on a motorcycle. This place was equipped with a beautiful outdoor firepit, 2 gas propane grills, and an indoor propane heater (leave the door cracked). The showers are located at the house on the property and were very clean. There's a...
United States
Ian
$140 nightly
The price is $152
Jun 30 - Jul 1
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
$182 nightly
The price is $206
Jun 30 - Jul 1
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
$75 nightly
The price is $81
Jun 30 - Jul 1
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
Smart TV

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

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
$170 nightly
The price is $189
Jun 30 - Jul 1
Total with taxes and fees
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Exterior

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

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$161 nightly
The price is $180
Jun 30 - Jul 1
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (79 reviews)
"We have stayed here several times and it is always perfect. The hosts are great and the house is perfect. "
United States
paul s.
$162 nightly
The price is $180
Jun 30 - Jul 1
Total with taxes and fees
comfort, luxury, privacy
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (46 reviews)
"The property was beautiful and it truly felt like an escape. I"
United States
Kristina M.
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$191 nightly
The price is $213
Jul 1 - Jul 2
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$279 nightly
The price is $312
Jul 17 - Jul 18
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (18 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
Hiking Trails On-Site: Cozy Falls Brook Cabin
Smart TV, fireplace, video games, DVD player

Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (59 reviews)
"Great communication by owners. House was charming with plenty of room for a large family."
United States
Kathleen S.
$720 nightly
The price is $814
Jun 30 - Jul 1
Total with taxes and fees
Walk To Town, Hottub, Firepit, Games, Mt Snow
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$356 nightly
The price is $402
Jun 30 - Jul 1
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (50 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
$555 nightly
The price is $620
Jul 1 - Jul 2
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
$845 nightly
The price is $940
Jul 7 - Jul 8
Total with taxes and fees
Riverbend Berkshire East Basecamp - 3 bedrooms available
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
$622 nightly
The price is $695
Jun 30 - Jul 1
Total with taxes and fees
5BR Berkshire Home Mins To The Mountain
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 Greenfield Hotel Reviews

Hotel UMass

Hotel UMass

10/10 Excellent
"good"
Fanshuhan 1-night trip
Posted 1 hour ago
Hotel UMass

Find out more about Greenfield

Everything you need to know about Greenfield 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 Greenfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Greenfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greenfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenfield rentals

At Expedia, we put the best Greenfield 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 Greenfield 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 Greenfield 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 Greenfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Greenfield?

Yes, we have vacation rentals close to the most popular attractions 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 vacation home rentals that Greenfield has to offer?

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts: This vacation home rental outside of Greenfield is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Greenfield?

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

What are vacation rentals like in Greenfield?

Vacation rentals are privately owned properties you can book for several days or longer in Greenfield. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip.