Photo by Ed Gaffny

Greenfield Holiday Rentals

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Our top choices for Greenfield holiday rentals

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is NZ$346
includes taxes & fees
5 Jan - 6 Jan 2026
Lovely 2nd Floor Apartment
9.2 out of 10, Wonderful, (5)
"Room was clean and welcoming. Very close to grocery store and stores. Recommended it to my friend who will also be staying there. "
United States
Roddy
The price is NZ$401
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is NZ$441
includes taxes & fees
15 Jan - 16 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is NZ$525
includes taxes & fees
2 Jan - 3 Jan 2026
Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
The price is NZ$462
includes taxes & fees
11 Jan - 12 Jan 2026
Beautiful 2-bedroom cottage on Robert Frost Trail
10.0 out of 10, Exceptional, (1)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is NZ$814
includes taxes & fees
12 Jan - 13 Jan 2026
Terrific 3-bedroom unit in charming Leverett with AC
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is NZ$727
includes taxes & fees
3 Jan - 4 Jan 2026
Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (2)
"as advertised."
United States
Joshua G.
The price is NZ$1,291
includes taxes & fees
13 Jan - 14 Jan 2026
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
10.0 out of 10, Exceptional, (8)
"Thanks for a great stay"
United States
Andrea M.
The price is NZ$1,302
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Valley View Post & Beam Villa!
The price is NZ$281
includes taxes & fees
4 Jan - 5 Jan 2026
2 Twin beds on 1st floor with En-suite bathroom.

Holiday Home in Amherst

Luxury Retreat inAmherst
10.0 out of 10, Exceptional, (1)
"Very helpful and easy communication. Very clean and nice place. We were very busy and only really were at the place to sleep but it is quiet and perfect for a restful stay."
United States
Robert
The price is NZ$1,443
includes taxes & fees
1 Jan - 2 Jan 2026
Luxury Retreat inAmherst
9.2 out of 10, Wonderful, (19)
"Great property! Thank you for a wonderful stay."
United States
David
The price is NZ$725
includes taxes & fees
1 Jan - 2 Jan 2026
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
2.0 star property
The price is NZ$881
includes taxes & fees
5 Jan - 6 Jan 2026
Secluded Vermont Chalet w/ Sweeping Mountain Views

Cabin in Charlemont

Bear Creek Cabin
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,031
includes taxes & fees
11 Jan - 12 Jan 2026
Bear Creek Cabin
10.0 out of 10, Exceptional, (2)
"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$1,039
includes taxes & fees
12 Jan - 13 Jan 2026
Button's Modern Luxury Walkup Downtown Northampton
10.0 out of 10, Exceptional, (7)
"We stayed here to move our daughter into Smith, and it was a great property in a beautiful area. Debra was incredibly responsive and helpful and made a stressful time much easier."
United States
Lindsay R.
Historic downtown house. Unscented products and sustainability practices.
10.0 out of 10, Exceptional, (14)
"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$1,068
includes taxes & fees
12 Jan - 13 Jan 2026
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
2.0 star property
The price is NZ$1,120
includes taxes & fees
5 Jan - 6 Jan 2026
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
10.0 out of 10, Exceptional, (8)
"Amazing house"
United States
Anonymous traveller
The price is NZ$2,984
includes taxes & fees
9 Jan - 10 Jan 2026
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
2.0 star property
The price is NZ$1,143
includes taxes & fees
4 Jan - 5 Jan 2026
Berkshire East Basecamp - 5 bedroom Winter Vintage Vibe Retreat
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$346 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?

Secluded Family Getaway w/ On-Site Creek in Hawley: This holiday home rental outside of Greenfield is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Greenfield?

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

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.