A river winding through a valley with autumn foliage, surrounded by fields and distant hills.

Deerfield Holiday Rentals

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Our top choices for Deerfield holiday rentals

1. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (61 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is NZ$342
includes taxes & fees
18 Aug - 19 Aug
Lovely 2nd Floor Apartment

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
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is NZ$471
includes taxes & fees
9 Sept - 10 Sept
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

3. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is NZ$348
includes taxes & fees
24 Aug - 25 Aug
Balcony Room in Victorian Home private bath

4. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is NZ$359
includes taxes & fees
31 Aug - 1 Sept
Private bed with En-suite bathroom Marigold Room

5. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is NZ$602
includes taxes & fees
13 Aug - 14 Aug
Cozy private 2 bed apartment in Shelburne Falls

6. 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, (10 reviews)
"Nice place"
United States
Tom
The price is NZ$484
includes taxes & fees
16 Aug - 17 Aug
Light-filled treetop apartment close to downtown Greenfield and Highland Park

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, (17 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is NZ$267
includes taxes & fees
20 Aug - 21 Aug
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

8. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is NZ$328
includes taxes & fees
27 Aug - 28 Aug
Rose room Victorian home queen bed private bath

9. 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$332
includes taxes & fees
17 Aug - 18 Aug
2 Twin beds on 1st floor with En-suite bathroom.

10. 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, (33 reviews)
"We had a lovely weekend, it was quiet, private and watching the horses in the pasture was wonderful. We would definitely stay again. "
United States
Kim G.
The price is NZ$397
includes taxes & fees
18 Aug - 19 Aug
Serene 1-bedroom suite on 75 acre horse property

11. 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$748
includes taxes & fees
8 Sept - 9 Sept
Spacious & Cozy Ground Floor 2/3 Bed private suite

12. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is NZ$138
includes taxes & fees
15 Aug - 16 Aug
2 private mountain RV pads for rent. Full hook ups

13. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (34 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is NZ$358
includes taxes & fees
13 Aug - 14 Aug
Newly Built Barn Loft in Pioneer Valley

14. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 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.
The price is NZ$750
includes taxes & fees
7 Sept - 8 Sept
Stunning Glass House nestled in the Vermont wilderness!

15. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (53 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is NZ$1,231
includes taxes & fees
16 Aug - 17 Aug
Spacious 5BR w/ Hot Tub & Games

16. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveller
The price is NZ$695
includes taxes & fees
31 Aug - 1 Sept
Charming, updated 3 bedroom farmhouse farm stay.

17. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is NZ$561
includes taxes & fees
18 Aug - 19 Aug
Vikings Villages Resort - Double Bed Room

18. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is NZ$796
includes taxes & fees
28 Aug - 29 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available

19. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (6 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$845
includes taxes & fees
17 Aug - 18 Aug
Button's Modern Luxury Walkup Downtown Northampton

20. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (6 reviews)
"It was a very pleasant & peaceful night! They were very pleasant, helpful & very detailed when giving all the information/instructions on how to check in & how to use the incinerator toilet! Places to eat ,hike etc…."
United States
Julie
The price is NZ$225
includes taxes & fees
24 Aug - 25 Aug
Yurt Oasis in the woods of Hinsdale, NH
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 Deerfield Hotel Reviews

Find out more about Deerfield

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Deerfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Deerfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Deerfield. Seeing all the best attractions is bound to make you fall in love with Deerfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Deerfield short-term rentals, that won’t be hard to do.

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.