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

Holiday Rentals in Greenfield

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Greenfield holiday 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.
The price is €204
includes taxes & fees
4 Nov - 5 Nov
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, (70 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is €230
includes taxes & fees
25 Oct - 26 Oct
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
The price is €234
includes taxes & fees
26 Oct - 27 Oct
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
The price is €164
includes taxes & fees
4 Nov - 5 Nov
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 bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is €188
includes taxes & fees
15 Nov - 16 Nov
Private bed with En-suite bathroom Marigold Room
A living room with a beige sofa, a patterned rug, and a wooden floor.

6. 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 €328
includes taxes & fees
18 Nov - 19 Nov
Spacious & Cozy Ground Floor 2/3 Bed private suite
A kitchen with wooden cabinets, a stainless steel dishwasher, and a dining table with benches.

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

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
The price is €282
includes taxes & fees
27 Oct - 28 Oct
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A hallway with wooden flooring, white walls, and a bed in the background.

8. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"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 €374
includes taxes & fees
22 Oct - 23 Oct
Cozy private 2 bed apartment in Shelburne Falls
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

9. 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 €178
includes taxes & fees
22 Oct - 23 Oct
Rose room Victorian home queen bed private bath
Room

10. Queen Bedroom in Victorian Home private bath.

Queen Bedroom in Victorian Home private bath.
Shelburne Falls
The price is €181
includes taxes & fees
16 Nov - 17 Nov
Queen Bedroom in Victorian Home private bath.
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 is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is €604
includes taxes & fees
22 Oct - 23 Oct
Spacious 5BR w/ Hot Tub & Games
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

12. 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.
Stunning Glass House nestled in the Vermont wilderness!
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

13. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
Cozy Vermont Tiny Home Get Away
A rustic cabin with a covered porch, a small shed, and outdoor seating.

14. 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, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is €144
includes taxes & fees
25 Oct - 26 Oct
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

15. 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 €387
includes taxes & fees
21 Nov - 22 Nov
Charming, updated 3 bedroom farmhouse farm stay.
A table with chairs on an outdoor deck, overlooking a forested area with hills in the distance.

16. 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, (1 review)
"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 €439
includes taxes & fees
1 Nov - 2 Nov
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
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 €313
includes taxes & fees
27 Oct - 28 Oct
Vikings Villages Resort - Double Bed Room
A bedroom with a bed, dresser, mirror, and a cabinet with glass doors.

18. 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.
The price is €624
includes taxes & fees
27 Oct - 28 Oct
Penthouse overlooking downtown Amherst!
A lakeside residential area with houses along the water's edge, a dock, and a boat.

19. 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 €623
includes taxes & fees
1 Nov - 2 Nov
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
A bedroom with a large bed, a nightstand with a lamp, a dresser, and a window with blinds.

20. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
The price is €384
includes taxes & fees
22 Oct - 23 Oct
A Cozy Condo Near Horse Farm + Mount Sugarloaf
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 Northampton

Hotel Northampton

10/10 Excellent
"great place and location. twice I felt like I was about to be kicked out, before they realized I was a guest, so that didn't feel great. I can hazard a guess as to why. other than that it's a great building."
Anna 1-night trip
Posted 4 hours ago
Hotel Northampton

Find out more about Greenfield

Everything you need to know about Greenfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Greenfield holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenfield holiday rentals we have selected for you start as low as €134 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 holiday 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 holiday.

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 holiday rentals in Greenfield?

Yes, there are holiday rentals close to the most popular sights 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 holiday rentals that Greenfield has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday 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 holiday rentals like in Greenfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenfield. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.