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Holiday Homes in Williamsburg

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Williamsburg holiday homes

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

1. 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$734
includes taxes & fees
20 Sept - 21 Sept
Charming, updated 3 bedroom farmhouse farm stay.
A cozy room with two beds, large windows, and a view of a snowy landscape.

2. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (77 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is NZ$470
includes taxes & fees
21 Sept - 22 Sept
The Creation Station is a cozy place so make yourself at home.
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

3. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (65 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$349
includes taxes & fees
20 Sept - 21 Sept
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.

4. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is NZ$367
includes taxes & fees
28 Sept - 29 Sept
Private bed with En-suite bathroom Marigold Room
A hallway with wooden flooring, white walls, and a bed in the background.

5. 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 NZ$615
includes taxes & fees
20 Sept - 21 Sept
Cozy private 2 bed apartment in Shelburne Falls
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

6. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is NZ$493
includes taxes & fees
27 Sept - 28 Sept
Real Estate: Therapy - Lake, Laundry, Love it
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$636
includes taxes & fees
29 Sept - 30 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A bedroom with a bed, curtains, a bedside table, and a lamp.

8. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is NZ$772
includes taxes & fees
28 Sept - 29 Sept
Townhouse with Pool Table - Renovated w/ King Bed
A house with a porch, a garden with pink flowers, and a stone wall along the road.

9. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (151 reviews)
"Great location"
United States
Will G.
The price is NZ$600
includes taxes & fees
22 Sept - 23 Sept
Big farmhouse in the foothills of the Berkshires
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

10. 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.
Spacious 5BR w/ Hot Tub & Games
A hot tub with a string of lights above it, set against a dark night sky.

11. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$681
includes taxes & fees
29 Sept - 30 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

12. Spacious Holyoke Home: Work, Play & Unwind!

Spacious Holyoke Home: Work, Play & Unwind!
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"This was a beautiful place to stay and was perfect for our needs. It was very clean and we enjoyed our stay. We didn't realize the house had three separate areas but it worked out well for our dance competition in Springfield."
United States
Celeste D.
The price is NZ$3,044
includes taxes & fees
29 Sept - 30 Sept
Spacious Holyoke Home: Work, Play & Unwind!
An aerial view of a house surrounded by a forest with autumn foliage.

13. 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 NZ$922
includes taxes & fees
22 Sept - 23 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

14. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The Greylock Cabin
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 Williamsburg Hotel Reviews

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Wonderful, courteous and helpful staff, clean room and incredibly quiet considering the convenient proximity of I-90! Several places w/in walking distance for dining. Nice pool and gym, delicious complimentary breakfast with actual good Lavazza coffee!! Woot! Woot!!"
Elise 1-night trip
Posted 5 hours ago
Tru by Hilton Chicopee Springfield

Find out more about Williamsburg

Williamsburg Holiday Homes information

Number of reviews
217
Accommodation
135 Holiday Homes
Lowest Price
NZ$349
Highest Price
NZ$3,044