Williamsburg Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Williamsburg holiday 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 NZ$719
includes taxes & fees
6 Dec - 7 Dec
Charming, updated 3 bedroom farmhouse farm stay.
A spacious dining area with a wooden table, chairs, and a potted plant.

2. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (13 reviews)
"Incredible house! A little tricky to find but worth it once you’re there. Very spacious, vaulted ceilings, and the view is unmatched. You can see more than 10 miles, with the city in the distance, and if you’re lucky, a storm with shows of lightning and thunder (our LA kids were wowed). Huge backyard, many bedrooms, and lots of hangout areas. A great retreat from it all."
United States
Andrew K.
The price is NZ$1,073
includes taxes & fees
18 Nov - 19 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 NZ$847
includes taxes & fees
17 Nov - 18 Nov
Button's Modern Luxury Walkup Downtown Northampton
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

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

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
10.0 out of 10, Exceptional, (1 review)
"Great place! Very clean!"
United States
Sherry T.
The price is NZ$601
includes taxes & fees
22 Nov - 23 Nov
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A hot tub on a wooden deck with snow on the ground and trees in the background.

5. 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 NZ$479
includes taxes & fees
18 Nov - 19 Nov
The Creation Station is a cozy place so make yourself at home.
A television displaying a coastal scene, a window with a view of buildings, and a sign reading 'CAPE COD'.

6. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (2 reviews)
"Great space. Great location."
United States
Mike S.
The price is NZ$976
includes taxes & fees
16 Nov - 17 Nov
Penthouse overlooking downtown Amherst!
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

7. 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 NZ$406
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A covered porch with white railings, two wicker chairs, and potted plants.

8. 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, (15 reviews)
"Nice place"
United States
Tom
The price is NZ$491
includes taxes & fees
17 Nov - 18 Nov
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A wooden door with a mirror, a small basket with dried flowers, and a light switch on the wall.

9. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (74 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is NZ$429
includes taxes & fees
17 Nov - 18 Nov
Lovely 2nd Floor Apartment
A hallway with wooden paneling, a Monopoly board game on a shelf, and decorative vases.

10. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
The price is NZ$780
includes taxes & fees
16 Nov - 17 Nov
A Cozy Condo Near Horse Farm + Mount Sugarloaf
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
3.0 star property
Holyoke
The price is NZ$421
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A blue house with a porch, a wooden bench, and a door.

12. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – 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 NZ$407
includes taxes & fees
18 Nov - 19 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A gazebo with seating, surrounded by a fenced area with trees and a clear sky.

13. 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, (41 reviews)
"We had a great, restorative stay in Liberty Woods. It is a lovely oasis with kind humans, friendly animals and beautiful horses in a beautiful setting."
United States
Anna O.
Serene 1-bedroom suite on 75 acre horse property
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a pool table.

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (20 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is NZ$743
includes taxes & fees
16 Nov - 17 Nov
Townhouse with Pool Table - Renovated w/ King Bed
A two-story residential building with a sign indicating 'Victory Residence' and the address '1785'.

15. 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 NZ$524
includes taxes & fees
22 Nov - 23 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center
A two-story house with a front porch, a concrete walkway, and a well-maintained lawn.

16. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is NZ$594
includes taxes & fees
27 Nov - 28 Nov
Cozy Home in Holyoke with 3 bedrooms
A modern kitchen with white cabinets, a black stove, and a large window.

17. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 reviews)
"Great place for a couple to stay. Hostess was fantastic. We had everything we needed. Would definitely recommend and would stay again!"
United States
Doreen R.
The price is NZ$411
includes taxes & fees
16 Nov - 17 Nov
Newly Built Barn Loft in Pioneer Valley
A room with a green floor, a white door, and a window with blinds.

18. 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 NZ$615
includes taxes & fees
29 Nov - 30 Nov
Spacious & Cozy Ground Floor 2/3 Bed private suite
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

19. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is NZ$309
includes taxes & fees
17 Nov - 18 Nov
2 Twin beds on 1st floor with En-suite bathroom.
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

20. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is NZ$770
includes taxes & fees
16 Nov - 17 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
Hotel Northampton

Hotel Northampton

Hotel Northampton
Northampton

10/10 Excellent

Great property. Large room, great shower. Really clean.
Australia
Aimee
Reviewed September 11, 2024
Hotel Northampton

Find out more about Williamsburg

Everything you need to know about Williamsburg 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 Williamsburg 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 Williamsburg holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Williamsburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Williamsburg. 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 Williamsburg 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 Williamsburg holiday rentals we have selected for you start as low as NZ$309 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Williamsburg rentals

At Expedia, we put the best Williamsburg 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 Williamsburg 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 Williamsburg 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 Williamsburg. 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

Can I find holiday rentals in Williamsburg?

Yes, there are holiday rentals close to the most popular sights in Williamsburg, or you can select a more secluded option if you're looking for a relaxing stay. Williamsburg is known for its restaurants and shopping.

What are some of the best holiday rentals that Williamsburg has to offer?

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

How many holiday rentals are there in Williamsburg?

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

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 holiday rentals like in Williamsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Williamsburg. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips.