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
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 blue house with a porch, a wooden bench, and a door.

1. 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.
$205 nightly
The price is $229
Nov 18 - Nov 19
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

2. 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
$213 nightly
The price is $238
Nov 17 - Nov 18
Total with taxes and fees
Lovely 2nd Floor Apartment
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
$244 nightly
The price is $273
Nov 17 - Nov 18
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

4. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$153 nightly
The price is $171
Nov 15 - Nov 16
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

5. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
$177 nightly
The price is $198
Nov 15 - Nov 16
Total with taxes and fees
Private room with En-suite bathroom Marigold Room
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

6. 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.
$259 nightly
The price is $289
Nov 16 - Nov 17
Total with taxes and fees
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
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
$353 nightly
The price is $395
Nov 15 - Nov 16
Total with taxes and fees
Shelburne Falls on Main
A living room with a beige sofa, a patterned rug, and a wooden floor.

8. 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.
$310 nightly
The price is $346
Nov 15 - Nov 16
Total with taxes and fees
Spacious & Cozy Ground Floor 2/3 Bed private suite
A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

9. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$137 nightly
The price is $149
Nov 17 - Nov 18
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

10. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
$84 nightly
The price is $95
Nov 30 - Dec 1
Total with taxes and fees
Cozy Vermont Tiny Home Get Away
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

11. 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.
$570 nightly
The price is $637
Nov 17 - Nov 18
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

12. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$320 nightly
The price is $323
Nov 15 - Nov 16
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

13. 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.
$376 nightly
The price is $397
Dec 6 - Dec 7
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

14. 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.
$485 nightly
The price is $542
Nov 15 - Nov 16
Total with taxes and fees
Penthouse overlooking downtown Amherst!
A modern two-story house with large windows and a balcony.

15. 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.
$543 nightly
The price is $607
Nov 16 - Nov 17
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
A lakeside residential area with houses along the water's edge, a dock, and a boat.

16. 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.
$690 nightly
The price is $770
Nov 16 - Nov 17
Total with taxes and fees
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
A modern kitchen with a central island, bar stools, and a bicycle.

17. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
$426 nightly
The price is $476
Nov 17 - Nov 18
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
A wooden interior with a kitchen, bar area, and dining space.

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

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (9 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.
$201 nightly
The price is $225
Nov 18 - Nov 19
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

19. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.4 out of 10, Very good, (7 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
$547 nightly
The price is $613
Nov 14 - Nov 15
Total with taxes and fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A house with a garage, surrounded by snow-covered trees and a mountain in the background.

20. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (16 reviews)
"Very peaceful backyard!! Great back deck!!"
United States
Jacqueline M.
$436 nightly
The price is $488
Nov 17 - Nov 18
Total with taxes and fees
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
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

The Ellery

The Ellery

8/10 Good
"We have stayed at the Ellery several times. The building is old so the decor is more traditional with no overhead lights making the rooms rather dark (I had to fumble to find the light switches on the lamps). The mattress and bedding were very comfortable although the bed frame was a bit high for a petite person. The best part of our stay was the breakfast room with a lovely tea selection (day or night) and really nice breakfast options. We appreciated the fruit filled water container and cookies in the lobby."
Susan 1-night trip
Posted 2 hours ago
The Ellery

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 $95 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?

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.