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

Holiday Homes in Greenfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Greenfield holiday homes

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

1. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 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 AU$332
includes taxes & fees
22 Oct - 23 Oct
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

2. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AU$310
includes taxes & fees
28 Oct - 29 Oct
Private bed with En-suite bathroom Marigold Room
A bedroom with a skylight, a bed with floral bedding, a bedside table, and a nightstand.

3. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is AU$152
includes taxes & fees
30 Oct - 31 Oct
Cozy Vermont Tiny Home Get Away
A hallway with wooden flooring, white walls, and a bed in the background.

4. 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 AU$603
includes taxes & fees
5 Oct - 6 Oct
Cozy private 2 bed apartment in Shelburne Falls
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

5. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 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 AU$1,126
includes taxes & fees
15 Oct - 16 Oct
Spacious 5BR w/ Hot Tub & Games
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

6. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 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 AU$630
includes taxes & fees
5 Oct - 6 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

7. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
5BR Berkshire Home Mins To The Mountain
An aerial view of a house surrounded by a forest with autumn foliage.

8. 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, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is AU$785
includes taxes & fees
28 Oct - 29 Oct
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

9. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AU$286
includes taxes & fees
12 Oct - 13 Oct
The Eagles Wing at The CHM - Private Apartment
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

10. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is AU$981
includes taxes & fees
27 Oct - 28 Oct
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

11. 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, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is AU$793
includes taxes & fees
26 Oct - 27 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

12. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and a terrific central location for all things outdoors."
United States
Alex B.
The price is AU$1,092
includes taxes & fees
9 Oct - 10 Oct
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

13. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is AU$1,108
includes taxes & fees
6 Oct - 7 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greenfield Hotel Reviews

The White House Inn

The White House Inn

10/10 Excellent
"Excellent place to stay. This was our second visit. Amazing and friendly staff, amazing food at Restuarant, very comfortable bed, extremely clean room, and very nice breakfast! We will definitely come back!"
Paul 2-night trip
Posted 7 hours ago
The White House Inn

Find out more about Greenfield

Greenfield Holiday Homes information

Number of reviews
283
Accommodation
191 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$1,126