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Deerfield Holiday Rentals

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Check prices for these dates

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

Our top choices for Deerfield 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 NZ$395
includes taxes & fees
11 Nov - 12 Nov
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.

2. 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 NZ$478
includes taxes & fees
12 Nov - 13 Nov
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.

3. 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 NZ$308
includes taxes & fees
15 Nov - 16 Nov
2 Twin beds on 1st floor with En-suite bathroom.
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

4. 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
The price is NZ$418
includes taxes & fees
19 Nov - 20 Nov
Lovely 2nd Floor Apartment
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

5. 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 NZ$534
includes taxes & fees
17 Nov - 18 Nov
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

6. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is NZ$349
includes taxes & fees
12 Nov - 13 Nov
Private room with En-suite bathroom Marigold Room
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

7. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is NZ$338
includes taxes & fees
11 Nov - 12 Nov
Balcony Room in Victorian Home private bath
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

8. 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 NZ$331
includes taxes & fees
11 Nov - 12 Nov
Rose room Victorian home queen bed private bath
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.
The price is NZ$619
includes taxes & fees
11 Nov - 12 Nov
Spacious & Cozy Ground Floor 2/3 Bed private suite
A hallway with wooden flooring, white walls, and a bed in the background.

10. 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 NZ$702
includes taxes & fees
24 Nov - 25 Nov
Shelburne Falls on Main
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

11. 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 NZ$705
includes taxes & fees
6 Dec - 7 Dec
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.

12. 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 NZ$890
includes taxes & fees
11 Nov - 12 Nov
Penthouse overlooking downtown Amherst!
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

13. 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.
The price is NZ$168
includes taxes & fees
30 Nov - 1 Dec
Cozy Vermont Tiny Home Get Away
A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

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, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is NZ$279
includes taxes & fees
12 Nov - 13 Nov
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
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
The price is NZ$831
includes taxes & fees
17 Nov - 18 Nov
Button's Modern Luxury Walkup Downtown Northampton
A modern living room with a sofa, a coffee table, and a fireplace.

16. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
The price is NZ$778
includes taxes & fees
11 Nov - 12 Nov
A Cozy Condo Near Horse Farm + Mount Sugarloaf
A modern two-story house with large windows and a balcony.

17. 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 NZ$1,064
includes taxes & fees
11 Nov - 12 Nov
Cozy Valley View Post & Beam Villa!
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

18. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (40 reviews)
"We had a great, restorative stay in Liberty Woods. It is a lovely oasis with kind humans, friendly animals and beautiful horses in a beautiful setting."
United States
Anna O.
The price is NZ$450
includes taxes & fees
30 Nov - 1 Dec
Serene 1-bedroom suite on 75 acre horse property
A room with a large window overlooking a lake at sunset.

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 NZ$1,344
includes taxes & fees
16 Nov - 17 Nov
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
A spacious kitchen with wooden flooring, a central island with stools, a dining table, and pendant lighting.

20. 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
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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Find holiday rentals that suit your style

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Top Deerfield 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

Quaint and comfortable escape in a quiet village
Australia
Adam
Reviewed March 26, 2025
Blooming Inn

Find out more about Deerfield

Everything you need to know about Deerfield 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 Deerfield holiday rental for you. At Expedia, you can take your pick from private holiday 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 Deerfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Deerfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Deerfield. 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 Deerfield 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 Deerfield holiday rentals we have selected for you start as low as NZ$168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Deerfield rentals

At Expedia, we put the best Deerfield 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 Deerfield 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 Deerfield 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 Deerfield. 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

Can I find a holiday rental in Deerfield?

Yes, there are holiday rentals in Deerfield close to Richardson's Candy Kitchen, or you can select a more secluded option if you're looking for a relaxing stay. Deerfield is known for its bars and monuments. Make sure you have time to check out the churches and architecture during your trip.

What are some of the best holiday rentals that Deerfield has to offer?

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

What’s there to see and do in Deerfield?

Deerfield River and Connecticut River are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Richardson's Candy Kitchen. While here, Historic Deerfield Village and Memorial Hall Museum are other places worth a visit.

What’s a holiday rental in Deerfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Deerfield. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.