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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
$197 nightly
The price is $220
Nov 9 - Nov 10
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, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
$213 nightly
The price is $238
Nov 1 - Nov 2
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
$243 nightly
The price is $271
Nov 1 - Nov 2
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 1 - Nov 2
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 9 - Nov 10
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
$259 nightly
The price is $289
Nov 2 - Nov 3
Total with taxes and fees
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

7. 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, (20 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$142 nightly
The price is $155
Nov 2 - Nov 3
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A hallway with wooden flooring, white walls, and a bed in the background.

8. 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
$354 nightly
The price is $396
Nov 1 - Nov 2
Total with taxes and fees
Shelburne Falls on Main
A living room with a beige sofa, a patterned rug, and a wooden floor.

9. 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.
$308 nightly
The price is $344
Nov 1 - Nov 2
Total with taxes and fees
Spacious & Cozy Ground Floor 2/3 Bed private suite
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

10. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (1 review)
"Great space. Great location."
United States
Mike S.
$450 nightly
The price is $503
Nov 1 - Nov 2
Total with taxes and fees
Penthouse overlooking downtown Amherst!
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

11. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
$400 nightly
The price is $448
Nov 8 - Nov 9
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

12. 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.
$558 nightly
The price is $624
Nov 2 - Nov 3
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
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.
$400 nightly
The price is $423
Nov 2 - Nov 3
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
A lakeside park with picnic tables and a concrete walkway.

14. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
$67 nightly
The price is $73
Nov 1 - Nov 2
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
A modern kitchen with a central island, bar stools, and a bicycle.

15. 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 3 - Nov 4
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
A wooden interior with a kitchen, bar area, and dining space.

16. 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, (7 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.
$206 nightly
The price is $230
Nov 2 - Nov 3
Total with taxes and fees
The Studio with a View. Bring your dog, too!
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
$320 nightly
The price is $323
Nov 1 - Nov 2
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A modern two-story house with large windows and a balcony.

18. 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.
$542 nightly
The price is $605
Nov 2 - Nov 3
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
Property grounds

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.
$440 nightly
The price is $493
Nov 1 - Nov 2
Total with taxes and fees
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

20. 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.
$864 nightly
The price is $965
Nov 5 - Nov 6
Total with taxes and fees
Amherst -NEW - Campus Convenience & Social Privacy
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

Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

10/10 Excellent
"All was very good! Would definitely stay here again."
Tammy 1-night trip
Posted less than an hour ago
Fairfield Inn & Suites Springfield Northampton/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 $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.

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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.