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Williamsburg Holiday Rentals

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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 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, (41 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$618
includes taxes & fees
29 Sept - 30 Sept
Charming, updated 3 bedroom farmhouse farm stay.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

2. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (3 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 AU$350
includes taxes & fees
29 Sept - 30 Sept
Modern Studio Ideal for Traveling Professionals
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

3. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AU$339
includes taxes & fees
29 Sept - 30 Sept
Modern Studio Ideal for Traveling Professionals
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 AU$400
includes taxes & fees
29 Sept - 30 Sept
The Creation Station is a cozy place so make yourself at home.
Exterior

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

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
The price is AU$496
includes taxes & fees
29 Sept - 30 Sept
Work, Play & Stay! Apt Near Holyoke Medical Center
A blue house with a porch, a wooden bench, and a door.

6. 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
9.6 out of 10, Exceptional, (9 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is AU$349
includes taxes & fees
5 Oct - 6 Oct
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A modern kitchen with a central island, bar stools, and a bicycle.

7. 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 AU$701
includes taxes & fees
5 Oct - 6 Oct
Button's Modern Luxury Walkup Downtown Northampton
A kitchen with wooden cabinets, a stainless steel dishwasher, and a dining table with benches.

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

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
The price is AU$461
includes taxes & fees
5 Oct - 6 Oct
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

9. 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 AU$291
includes taxes & fees
21 Oct - 22 Oct
2 Twin beds on 1st floor with En-suite bathroom.
A modern two-story house with large windows and a balcony.

10. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (12 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is AU$906
includes taxes & fees
29 Sept - 30 Sept
Cozy Valley View Post & Beam Villa!
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

11. 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$333
includes taxes & fees
22 Oct - 23 Oct
Lovely 2nd Floor Apartment
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.

12. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (38 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 AU$307
includes taxes & fees
29 Sept - 30 Sept
Newly Built Barn Loft in Pioneer Valley
A living room with a fireplace, a sofa, a coffee table, and a TV.

13. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (11 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AU$344
includes taxes & fees
29 Sept - 30 Sept
Cozy 2-bedroom apartment in Chicopee
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.

14. 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 AU$547
includes taxes & fees
7 Oct - 8 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A living room with a sofa set, a coffee table, and two lamps.

15. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (12 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
The price is AU$437
includes taxes & fees
29 Sept - 30 Sept
Cozy First Floor Apartment. Located in a quiet neighborhood.
A bedroom with a bed, curtains, a bedside table, and a lamp.

16. 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 AU$635
includes taxes & fees
29 Sept - 30 Sept
Townhouse with Pool Table - Renovated w/ King Bed
A living room with a beige sofa, a patterned rug, and a wooden floor.

17. 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 AU$527
includes taxes & fees
29 Sept - 30 Sept
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 large tree in the foreground.

18. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AU$307
includes taxes & fees
27 Oct - 28 Oct
Private bed with En-suite bathroom Marigold Room
A hallway with wooden flooring, white walls, and a bed in the background.

19. 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$597
includes taxes & fees
30 Sept - 1 Oct
Cozy private 2 bed apartment in Shelburne Falls
A house with a staircase leading to a porch, surrounded by snow and string lights.

20. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
10.0 out of 10, Exceptional, (12 reviews)
"Nice place"
United States
Tom
The price is AU$405
includes taxes & fees
29 Sept - 30 Sept
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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

Inn on Boltwood

Inn on Boltwood

10/10 Excellent
"I loved the property! The food and drinks were all fantastic!"
Sharie 2-night trip
Posted 1 hour ago
Inn on Boltwood

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 favourite 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 depend 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 AU$547 per night. Entering your travel dates in the search wizard might find you 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.