Williamsburg Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Williamsburg holiday rentals

Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow
Ludlow
8.4 out of 10, Very good, (9)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
United States
Matthew H.
The price is AU$229
includes taxes & fees
19 Dec - 20 Dec
Tiny Home with AC and WiFi in lovely Ludlow

Serene 1-bedroom suite on 65 acre horse property

Serene 1-bedroom suite on 65 acre horse property
Belchertown
10.0 out of 10, Exceptional, (23)
"A great jumping off point for the Pioneer Valley and 5 colleges. Brent and Claire were wonderful hosts! Nice and quiet on the property, and it’s a neat experience to have the beautiful horses right outside your window. "
United States
Claire W.
The price is AU$316
includes taxes & fees
22 Dec - 23 Dec
Serene 1-bedroom suite on 65 acre horse property

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (46)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is AU$306
includes taxes & fees
19 Dec - 20 Dec
Lovely 2nd Floor Apartment

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (12)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
United States
Eric W.
The price is AU$492
includes taxes & fees
21 Dec - 22 Dec
Cozy Home in Holyoke with 3 bedrooms

Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
The price is AU$410
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Chicopee Getaway

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
8.8 out of 10, Excellent, (3)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
The price is AU$314
includes taxes & fees
21 Dec - 22 Dec
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$570
includes taxes & fees
22 Dec - 23 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
2.0 star property
Belchertown
9.4 out of 10, Exceptional, (22)
"Adorable spot. Great location. Clean, organized and well stocked. "
United States
Jen M.
The price is AU$318
includes taxes & fees
19 Dec - 20 Dec
Newly Built Barn Loft in Pioneer Valley

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AU$588
includes taxes & fees
22 Dec - 23 Dec
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is AU$422
includes taxes & fees
22 Dec - 23 Dec
The Creation Station is a cozy place so make yourself at home.

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
United States
Matt G.
The price is AU$575
includes taxes & fees
19 Dec - 20 Dec
Townhouse with Pool Table - Renovated w/ King Bed

Couples 2 Bedroom Retreat-Close to Shelburne Falls

Couples 2 Bedroom Retreat-Close to Shelburne Falls
Colrain
10.0 out of 10, Exceptional, (4)
"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "
United States
KayKay S.
The price is AU$537
includes taxes & fees
21 Dec - 22 Dec
Couples 2 Bedroom Retreat-Close to Shelburne Falls

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
2.0 star property
Chicopee
10.0 out of 10, Exceptional, (1)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is AU$516
includes taxes & fees
22 Dec - 23 Dec
Welcoming 3-bedroom house- Gardner home

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Granby
9.0 out of 10, Wonderful, (22)
"Great overnight stay! "
United States
Carrie M.
The price is AU$407
includes taxes & fees
19 Dec - 20 Dec
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AU$517
includes taxes & fees
22 Dec - 23 Dec
Florida Mountain Log Cabin

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$230
includes taxes & fees
5 Jan - 6 Jan 2026
2 Twin beds on 1st floor with En-suite bathroom.

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, (34)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is AU$738
includes taxes & fees
21 Dec - 22 Dec
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (1)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AU$311
includes taxes & fees
20 Dec - 21 Dec
Cozy 2-bedroom apartment in Chicopee

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Amherst
9.4 out of 10, Exceptional, (18)
"Great property! Thank you for a wonderful stay."
United States
David
The price is AU$638
includes taxes & fees
21 Dec - 22 Dec
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is AU$554
includes taxes & fees
3 Jan - 4 Jan 2026
Big farmhouse in the foothills of the Berkshires
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Williamsburg Hotel Reviews

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$229 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?

Peace and quiet on the lake: This holiday home rental outside of Williamsburg is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Williamsburg?

Choose from 4 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.