Williamsburg Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Williamsburg vacation rentals

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, (44 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 AEDĀ 906
AEDĀ 1,455 total
includes taxes & fees
6 Dec - 7 Dec
Charming, updated 3 bedroom farmhouse farm stay.
A modern two-story house with large windows and a balcony.

2. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (13 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is AEDĀ 1,837
AEDĀ 2,224 total
includes taxes & fees
9 Nov - 10 Nov
Cozy Valley View Post & Beam Villa!
A modern kitchen with a central island, bar stools, and a bicycle.

3. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 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 AEDĀ 897
AEDĀ 1,748 total
includes taxes & fees
17 Nov - 18 Nov
Button's Modern Luxury Walkup Downtown Northampton
A cozy room with two beds, large windows, and a view of a snowy landscape.

4. 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, (79 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 AEDĀ 661
AEDĀ 976 total
includes taxes & fees
9 Nov - 10 Nov
The Creation Station is a cozy place so make yourself at home.
A modern living room with a sofa, a coffee table, and a fireplace.

5. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
The price is AEDĀ 793
AEDĀ 1,550 total
includes taxes & fees
8 Nov - 9 Nov
A Cozy Condo Near Horse Farm + Mount Sugarloaf
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

6. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (1 review)
"Great space. Great location."
United States
Mike S.
The price is AEDĀ 893
AEDĀ 1,777 total
includes taxes & fees
1 Dec - 2 Dec
Penthouse overlooking downtown Amherst!
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

7. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
The price is AEDĀ 456
AEDĀ 1,078 total
includes taxes & fees
9 Nov - 10 Nov
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

8. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is AEDĀ 562
AEDĀ 874 total
includes taxes & fees
8 Nov - 9 Nov
Lovely 2nd Floor Apartment
A house with a staircase leading to a porch, surrounded by snow and string lights.

9. 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, (13 reviews)
"Nice place"
United States
Tom
The price is AEDĀ 826
AEDĀ 1,001 total
includes taxes & fees
9 Nov - 10 Nov
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

10. Amherst -NEW - Campus Convenience & Social Privacy

Amherst -NEW - Campus Convenience & Social Privacy
Amherst
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic property and host. Left a suit accidentally and they were extremely accommodating in helping us get it back."
United States
Kimberly D.
The price is AEDĀ 3,068
AEDĀ 4,613 total
includes taxes & fees
18 Nov - 19 Nov
Amherst -NEW - Campus Convenience & Social Privacy
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

11. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is AEDĀ 209
AEDĀ 796 total
includes taxes & fees
8 Nov - 9 Nov
Modern Studio Ideal for Traveling Professionals
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

12. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (40 reviews)
"Not your average stay! This place is super cool!!"
United States
Wayne B.
The price is AEDĀ 551
AEDĀ 947 total
includes taxes & fees
30 Nov - 1 Dec
Serene 1-bedroom suite on 75 acre horse property
Exterior

13. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is AEDĀ 209
AEDĀ 1,050 total
includes taxes & fees
8 Nov - 9 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

14. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AEDĀ 316
AEDĀ 855 total
includes taxes & fees
8 Nov - 9 Nov
Modern Studio Ideal for Traveling Professionals
A blue house with a porch, a wooden bench, and a door.

15. Charming Country-Chic 1BR in Greenfield ā€“ King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield ā€“ King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is AEDĀ 321
AEDĀ 834 total
includes taxes & fees
11 Nov - 12 Nov
Charming Country-Chic 1BR in Greenfield ā€“ King Bed, Rain Shower, Near Berkshires
A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

16. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"Fantastic stay in Holyoke. House is close to town, well outfitted, and super clean. Easy check in process and great experience all around. "
United States
Grant J.
The price is AEDĀ 569
AEDĀ 1,260 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Home in Holyoke with 3 bedrooms
A bedroom with a bed, curtains, a bedside table, and a lamp.

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (18 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AEDĀ 737
AEDĀ 1,528 total
includes taxes & fees
9 Nov - 10 Nov
Townhouse with Pool Table - Renovated w/ King Bed
A modern living room with a leather sofa, a coffee table, and a dining table. There are two windows providing natural light, a ceiling light fixture, and a trash can.

18. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 reviews)
"The host was so responsive and made sure everything was perfect! It was the cutest and most comfy set up! With an adorable town beach 5 min down the road! Highly recommend!"
United States
Nora M.
The price is AEDĀ 661
AEDĀ 839 total
includes taxes & fees
8 Nov - 9 Nov
Newly Built Barn Loft in Pioneer Valley
A living room with a beige sofa, a patterned rug, and a wooden floor.

19. Spacious & Cozy Ground Floor 2/3 Bed private suite

Spacious & Cozy Ground Floor 2/3 Bed private suite
Shelburne Falls
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful property with an exceptional host!"
United States
Russ D.
The price is AEDĀ 591
AEDĀ 1,264 total
includes taxes & fees
8 Nov - 9 Nov
Spacious & Cozy Ground Floor 2/3 Bed private suite
A hallway with wooden flooring, white walls, and a bed in the background.

20. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
10.0 out of 10, Exceptional, (1 review)
"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 AEDĀ 739
AEDĀ 1,453 total
includes taxes & fees
8 Nov - 9 Nov
Shelburne Falls on Main
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

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
The Ellery

The Ellery

The Ellery
Northampton

10/10 Excellent

Itā€™s a great place to stay and we like the breakfast!
United States
Marilyn
Reviewed June 14, 2025
The Ellery

Frequently Asked Questions

Can I find vacation rentals in Williamsburg?

Yes, we give you a choice of vacation rentals near popular points of interest in Williamsburg, or you can choose a secluded option if you'd like a relaxing place to stay. Williamsburg is known for its restaurants and shopping.

What are some of the best vacation rentals in Williamsburg?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental near Williamsburg is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals are there in Williamsburg?

Choose from 5 Expedia vacation rentals in Williamsburg for a memorable vacation.

What can I see and do in Williamsburg?

Swift River and Petticoat Hill are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Brewer Brook Wildlife Management Area and Silvio O. Conte National Fish and Wildlife Refuge.

What are vacation rentals like in Williamsburg?

Vacation rentals are privately owned properties you can book for a short or long stay in Williamsburg. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.