Greenfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Greenfield vacation rentals

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

1. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (74 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is CA $217
CA $338 total
includes taxes & fees
Nov 17 - Nov 18
Lovely 2nd Floor Apartment
A blue house with a porch, a wooden bench, and a door.

2. 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
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is CA $127
CA $326 total
includes taxes & fees
Nov 18 - Nov 19
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A house with a staircase leading to a porch, surrounded by snow and string lights.

3. 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, (13 reviews)
"Nice place"
United States
Tom
The price is CA $319
CA $388 total
includes taxes & fees
Nov 17 - Nov 18
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A living room with a beige sofa, a patterned rug, and a wooden floor.

4. Spacious & Cozy Ground Floor 2/3 Bed private suite

Spacious & Cozy Ground Floor 2/3 Bed private suite
Shelburne Falls
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful property with an exceptional host!"
United States
Russ D.
The price is CA $228
CA $493 total
includes taxes & fees
Nov 15 - Nov 16
Spacious & Cozy Ground Floor 2/3 Bed private suite
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

5. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (56 reviews)
"This home was comfy, really clean and hosts were easy to reach and chat with during our stay. My extended family had a great time getting together this summer staying at hosts’ home!"
United States
Griffin S.
Spacious 5BR w/ Hot Tub & Games
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

6. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is CA $131
CA $244 total
includes taxes & fees
Nov 17 - Nov 18
2 Twin beds on 1st floor with En-suite bathroom.
A hallway with wooden flooring, white walls, and a bed in the background.

7. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
10.0 out of 10, Exceptional, (1 review)
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is CA $286
CA $561 total
includes taxes & fees
Nov 15 - Nov 16
Shelburne Falls on Main
A modern two-story house with large windows and a balcony.

8. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (13 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is CA $709
CA $860 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Valley View Post & Beam Villa!
A lakeside residential area with houses along the water's edge, a dock, and a boat.

9. 3br Lakefront Oasis in Shutesbury with central air and 180-deg views!

3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
Shutesbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time at the house. Perfect for family and young kids. Very clean. View of lake and bald eagles! were amazing. Host was very responsive and provided a lot of extra info on location places to eat, events, etc. Would definitely stay again."
United States
Tara I.
The price is CA $638
CA $1,093 total
includes taxes & fees
Nov 17 - Nov 18
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
A modern living room with a sofa, a coffee table, and a fireplace.

10. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
The price is CA $306
CA $629 total
includes taxes & fees
Nov 17 - Nov 18
A Cozy Condo Near Horse Farm + Mount Sugarloaf
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

11. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $163
CA $280 total
includes taxes & fees
Nov 15 - Nov 16
Private room with En-suite bathroom Marigold Room
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

12. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is CA $350
CA $565 total
includes taxes & fees
Dec 6 - Dec 7
Charming, updated 3 bedroom farmhouse farm stay.
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

13. Amherst -NEW - Campus Convenience & Social Privacy

Amherst -NEW - Campus Convenience & Social Privacy
Amherst
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic property and host. Left a suit accidentally and they were extremely accommodating in helping us get it back."
United States
Kimberly D.
The price is CA $1,190
CA $1,787 total
includes taxes & fees
Nov 18 - Nov 19
Amherst -NEW - Campus Convenience & Social Privacy
A wooden deck with a railing, a house with windows, and a forested area with a stream.

14. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The price is CA $603
CA $875 total
includes taxes & fees
Nov 15 - Nov 16
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

15. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
8.0 out of 10, Very good, (1 review)
"Very cute and welcoming B&B guest house. It was not clear to me that our private bathroom was across the hall. Some are and some not so check for that."
United States
Mikaela M.
The price is CA $147
CA $261 total
includes taxes & fees
Nov 14 - Nov 15
Rose room Victorian home queen bed private bath
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

16. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (2 reviews)
"Great space. Great location."
United States
Mike S.
The price is CA $345
CA $719 total
includes taxes & fees
Nov 19 - Nov 20
Penthouse overlooking downtown Amherst!
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

17. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is CA $390
CA $454 total
includes taxes & fees
Nov 15 - Nov 16
Vikings Villages Resort - Double Bed Room
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

18. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is CA $155
CA $270 total
includes taxes & fees
Nov 15 - Nov 16
Balcony Room in Victorian Home private bath
A log cabin with a deck, a fire pit, and an American flag.

19. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
10.0 out of 10, Exceptional, (2 reviews)
"This place was honestly amazing. All secluded and even with how far away the cabin was from the main road the cabin had everything you could imagine and everything felt perfect. 10/10 would return"
United States
Justin M.
The price is CA $272
CA $695 total
includes taxes & fees
Nov 17 - Nov 18
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

20. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
10.0 out of 10, Exceptional, (1 review)
"Great place! Very clean!"
United States
Sherry T.
The price is CA $168
CA $429 total
includes taxes & fees
Nov 16 - Nov 17
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
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

A two-story house with a porch, a balcony, and a chimney.
Blooming Inn

Blooming Inn

Blooming Inn
Shelburne Falls

10/10 Excellent

Amazing location lots of space to loung around and owners are very nice
Canada
Nathalie
Reviewed July 19, 2025
Blooming Inn

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenfield vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenfield vacation rentals we have selected for you start as low as CA $102 per night. Entering your travel dates in the search wizard 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.

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?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental outside of Greenfield is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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 Museum of Our Industrial Heritage.

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.