Williamsburg Holiday Homes from £167: Search Holiday Homes in Williamsburg

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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.

Williamsburg

Nancy M.

includes taxes & fees

4 Oct - 5 Oct

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.

Easthampton Ma.

Paula

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

3. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

includes taxes & fees

28 Sept - 29 Sept

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

4. Lovely 2nd Floor Apartment

Greenfield

Christa B.

includes taxes & fees

22 Oct - 23 Oct

A hallway with wooden flooring, white walls, and a bed in the background.

5. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bed, curtains, a bedside table, and a lamp.

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

Chicopee

Nicholas B.

includes taxes & fees

28 Sept - 29 Sept

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!

Sherwood Forest

Sharon K.

includes taxes & fees

28 Sept - 29 Sept

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

includes taxes & fees

29 Sept - 30 Sept

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

Russell

Will G.

includes taxes & fees

7 Oct - 8 Oct

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

includes taxes & fees

5 Oct - 6 Oct

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

11. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

12. Spacious 5BR w/ Hot Tub & Games

Colrain

Staci M.

includes taxes & fees

29 Sept - 30 Sept

A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

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

Holyoke

Celeste D.

includes taxes & fees

29 Sept - 30 Sept

An aerial view of a house surrounded by a forest with autumn foliage.

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

Whitingham

Jonathan

includes taxes & fees

27 Oct - 28 Oct

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

15. The Greylock Cabin

Florida

Margaret M.

includes taxes & fees

26 Oct - 27 Oct

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Top Williamsburg Hotel Reviews

D. Hotel Suites & Spa

10/10 Excellent

"Lovely stay, clean and comfy and we enjoyed the restaurant attached…however it was a little like dining in an Abercrombie store…very dark! But lovely food and reasonable prices. The hotel was nice and quiet too as out of town. Fabulous breakfast! Would definitely stay again."