Williamsburg Vacation Rentals

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Check prices for these dates

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Dec 20 - Dec 21
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Dec 21 - Dec 22
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Dec 26 - Dec 28
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Jan 2 - Jan 4

Our top choices for Williamsburg vacation rentals

Smart TV
Serene 1-bedroom suite on 65 acre horse property

Apartment in Belchertown

Serene 1-bedroom suite on 65 acre horse property
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 ￥15,775
￥32,683 total
includes taxes & fees
Dec 22 - Dec 23
Serene 1-bedroom suite on 65 acre horse property
Private kitchen
Tiny Home with AC and WiFi in lovely Ludlow

Vacation Home in Ludlow

Tiny Home with AC and WiFi in lovely 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 ￥12,462
￥23,612 total
includes taxes & fees
Dec 22 - Dec 23
Tiny Home with AC and WiFi in lovely Ludlow
TV
Charming Chicopee Getaway

Apartment in Chicopee

Charming Chicopee Getaway
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 ￥14,829
￥42,484 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop
Cozy Home in Holyoke with 3 bedrooms

Vacation Home in Holyoke

Cozy Home in Holyoke with 3 bedrooms
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 ￥20,508
￥50,044 total
includes taxes & fees
Dec 22 - Dec 23
Cozy Home in Holyoke with 3 bedrooms
Private kitchen
Welcoming 3-bedroom house- Gardner home

Vacation Home in Chicopee

Welcoming 3-bedroom house- Gardner home
2.0 star property
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 ￥18,930
￥53,334 total
includes taxes & fees
Dec 22 - Dec 23
Welcoming 3-bedroom house- Gardner home
Interior
Lovely 2nd Floor Apartment

Vacation Home in Greenfield

Lovely 2nd Floor Apartment
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 ￥18,315
￥31,736 total
includes taxes & fees
Dec 27 - Dec 28
Lovely 2nd Floor Apartment
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Apartment in Greenfield

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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 ￥10,222
￥32,563 total
includes taxes & fees
Dec 22 - Dec 23
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Desk, iron/ironing board, travel crib, WiFi
The Creation Station is a cozy place so make yourself at home.

Vacation Home in Easthampton Ma.

The Creation Station is a cozy place so make yourself at home.
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 ￥28,395
￥43,700 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Creation Station is a cozy place so make yourself at home.
Interior
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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 ￥23,000
￥58,994 total
includes taxes & fees
Dec 22 - Dec 23
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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 ￥25,272
￥61,002 total
includes taxes & fees
Dec 22 - Dec 23
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
TV
Florida Mountain Log Cabin

Vacation Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ￥28,987
￥53,476 total
includes taxes & fees
Dec 23 - Dec 24
Florida Mountain Log Cabin
Smart TV, books, stereo
Newly Built Barn Loft in Pioneer Valley

Apartment in Belchertown

Newly Built Barn Loft in Pioneer Valley
2.0 star property
9.4 out of 10, Exceptional, (22)
"Adorable spot. Great location. Clean, organized and well stocked. "
United States
Jen M.
The price is ￥24,846
￥33,099 total
includes taxes & fees
Dec 22 - Dec 23
Newly Built Barn Loft in Pioneer Valley
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

Apartment in Shelburne Falls

2 Twin beds on 1st floor with En-suite bathroom.
The price is ￥10,412
￥23,788 total
includes taxes & fees
Jan 5 - Jan 6, 2026
2 Twin beds on 1st floor with En-suite bathroom.
Game room
Couples 2 Bedroom Retreat-Close to Shelburne Falls

Vacation Home in Colrain

Couples 2 Bedroom Retreat-Close to Shelburne Falls
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 ￥24,372
￥55,592 total
includes taxes & fees
Dec 22 - Dec 23
Couples 2 Bedroom Retreat-Close to Shelburne Falls
3 bedrooms, desk, iron/ironing board, travel crib
Townhouse with Pool Table - Renovated w/ King Bed

Vacation Home in Chicopee

Townhouse with Pool Table - Renovated w/ King Bed
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 ￥28,395
￥60,492 total
includes taxes & fees
Dec 22 - Dec 23
Townhouse with Pool Table - Renovated w/ King Bed
Living area
Cozy 2-bedroom apartment in Chicopee

Apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
10.0 out of 10, Exceptional, (2)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is ￥21,927
￥32,214 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cozy 2-bedroom apartment in Chicopee
Living area
Penthouse Apartment on Park Street

Apartment in Adams

Penthouse Apartment on Park Street
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is ￥18,299
￥38,590 total
includes taxes & fees
Dec 23 - Dec 24
Penthouse Apartment on Park Street
Fridge, microwave, oven, stovetop
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Vacation Home in Granby

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
9.0 out of 10, Wonderful, (22)
"Great overnight stay! "
United States
Carrie M.
The price is ￥23,426
￥42,269 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Property grounds
Big farmhouse in the foothills of the Berkshires

Vacation Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ￥31,550
￥56,527 total
includes taxes & fees
Dec 22 - Dec 23
Big farmhouse in the foothills of the Berkshires
Property grounds
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 ￥36,283
￥78,412 total
includes taxes & fees
Jan 13 - Jan 14, 2026
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

Hotel Northampton

Hotel Northampton

10/10 Excellent
"Great, gracious hotel with old time charm. Clean and comfortable too."
Philip 1-night trip
Posted 6 hours ago
Hotel Northampton

Find out more about Williamsburg

Search for holiday rentals in Williamsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Williamsburg using one of the methods below:

  • View our selection of featured holiday rentals in Williamsburg
  • Use the map to find apartments and other holiday homes in the Williamsburg neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Williamsburg while they last

Look no further and take a look at our great range of rental properties in Williamsburg!

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?

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

How many vacation rentals are there in Williamsburg?

Choose from 4 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.