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

Greenfield Holiday Rentals

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Our top choices for Greenfield holiday rentals

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (58 reviews)
"Beautiful, thoughtful space on a gorgeous piece of property. "
United States
Jodi W.
The price is NZ$354
includes taxes & fees
13 July - 14 July
Lovely 2nd Floor Apartment

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, (8 reviews)
"We had a great"
United States
Meredith B.
The price is NZ$475
includes taxes & fees
8 July - 9 July
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

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, (6 reviews)
"Nice place"
United States
Tom
The price is NZ$447
includes taxes & fees
13 July - 14 July
Light-filled treetop apartment close to downtown Greenfield and Highland Park

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, (14 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is NZ$285
includes taxes & fees
17 July - 18 July
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

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$143
includes taxes & fees
2 July - 3 July
2 private mountain RV pads for rent. Full hook ups

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is NZ$762
includes taxes & fees
7 July - 8 July
Chalet Mount Snow/Stratton Skiing/hiking

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is NZ$334
includes taxes & fees
13 July - 14 July
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

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$317
includes taxes & fees
2 July - 3 July
2 Twin beds on 1st floor with En-suite bathroom.

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (79 reviews)
"We have stayed here several times and it is always perfect. The hosts are great and the house is perfect. "
United States
paul s.
The price is NZ$318
includes taxes & fees
2 July - 3 July
comfort, luxury, privacy

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is NZ$374
includes taxes & fees
5 July - 6 July
Private bed with En-suite bathroom Marigold Room

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is NZ$240
includes taxes & fees
2 July - 3 July
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is NZ$815
includes taxes & fees
6 July - 7 July
Stunning Glass House nestled in the Vermont wilderness!

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, (2 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.
The price is NZ$531
includes taxes & fees
6 July - 7 July
The Studio with a View. Bring your dog, too!

Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
The price is NZ$640
includes taxes & fees
6 July - 7 July
Shelburne Falls on Main

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is NZ$955
includes taxes & fees
8 July - 9 July
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

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$882
includes taxes & fees
14 July - 15 July
Button's Modern Luxury Walkup Downtown Northampton

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is NZ$582
includes taxes & fees
5 July - 6 July
Vikings Villages Resort - Double Bed Room

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (18 reviews)
"Great place!"
United States
Jack & Heather G.
The price is NZ$1,076
includes taxes & fees
21 July - 22 July
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,067
includes taxes & fees
7 July - 8 July
Bear Creek Cabin

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
The price is NZ$1,172
includes taxes & fees
7 July - 8 July
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
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

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, 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 NZ$240 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?

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts: This holiday home rental outside of Greenfield is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Greenfield?

Energy Park and Connecticut River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Poet's Seat Tower and Old Greenfield Village.

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.