Aerial view of Greenfield, Massachusetts in winter

Greenfield Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Greenfield vacation rentals

Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"We really enjoyed your place. It was clean and quiet, with some nice design touches. Beautiful woodwork coming up the stairs!! We used it for a self-crafted meditation retreat."
United States
E Kelly S.
$180 nightly
The price is $201
Jun 15 - Jun 16
Total with taxes and fees
Lovely 2nd Floor Apartment
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.
$210 nightly
The price is $234
Jun 16 - Jun 17
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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
$181 nightly
The price is $202
Jul 7 - Jul 8
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
10.0 out of 10, Exceptional, (3 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
$138 nightly
The price is $150
Jun 14 - Jun 15
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
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 13 - Jun 14
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.
$171 nightly
The price is $190
Jun 14 - Jun 15
Total with taxes and fees
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
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, (17 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.
$383 nightly
The price is $426
Jun 15 - Jun 16
Total with taxes and fees
Hiking Trails On-Site: Cozy Falls Brook Cabin
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (78 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 14 - Jun 15
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
$376 nightly
The price is $410
Jun 15 - Jun 16
Total with taxes and fees
Hiking Trails On-site: Cozy Falls Brook Cabin
Property grounds

Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts
Cummington
$128 nightly
The price is $135
Jun 13 - Jun 14
Total with taxes and fees
Unique and Eclectic Small Town Suite Rental in Massachusetts
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$190 nightly
The price is $212
Jun 14 - Jun 15
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
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.
$357 nightly
The price is $403
Jun 14 - Jun 15
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
$211 nightly
The price is $236
Jun 16 - Jun 17
Total with taxes and fees
Brookside cottage near the mountains and outdoor recreation
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
$173 nightly
The price is $193
Jun 14 - Jun 15
Total with taxes and fees
Rose room Victorian home queen bed private bath
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.
$180 nightly
The price is $203
Jun 30 - Jul 1
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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)
"Great location. Incredible outdoor space and comfortable furnishings."
United States
Debby B.
$404 nightly
The price is $453
Jun 29 - Jun 30
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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.
$265 nightly
The price is $297
Jun 22 - Jun 23
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$334 nightly
The price is $339
Jun 14 - Jun 15
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
House (3 Bedrooms) | Interior

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
$395 nightly
The price is $434
Jun 29 - Jun 30
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Dining

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (18 reviews)
"Great place!"
United States
Jack & Heather G.
$558 nightly
The price is $595
Jun 23 - Jun 24
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greenfield Hotel Reviews

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

10/10 Excellent
"There was an issue with our reservation and the front desk staff and management bent over backwards to help Expedia get the issue fixed. They saved our trip! Thank you so much!"
Jason 1-night trip
Posted 2 hours ago
Courtyard by Marriott Hadley Amherst

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 $158 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?

Kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley: This vacation home rental outside of Greenfield is located in the city center and offers a balcony, air-conditioning, and cable 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 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.