Williamsburg Holiday Rentals

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Holiday Rentals in Williamsburg

Cozy Cabin with fireplace, hot tub & hiking trails

7.4 out of 10, Good, (3)
"The property is amazing. Pictures do not do the gardens justice. The visiting horse and friendly cats were a plus. The pool is cloudy and needs more frequent cleaning than the weekly service due to its location under trees. The outdoor furniture also needs cleaning as do the dishes in the house. But you will hardly notice because the gardens are so well maintained and the hot tub works amazing."
Cozy Cabin with fireplace, hot tub & hiking trails

Newly renovated studio in Hagerstown--Self Check-in

10.0 out of 10, Exceptional, (25)
"Cute place. Property manager very responsive to needs. Great stay."
Newly renovated studio in Hagerstown--Self Check-in

Boho Bungalow off Main-one block from Lovely Park

9.4 out of 10, Exceptional, (6)
"My husband, son, and I stayed here the weekend of our daughter’s graduation from Miami University. It was so cute and easy to access. The communication was awesome and check in/check out process was simple. Would definitely recommend."
Boho Bungalow off Main-one block from Lovely Park

Exquisite Hagerstown Home with Deck & Gazebo!

10.0 out of 10, Exceptional, (4)
"This property was fantastic and had all the amenities we were looking for in a long weekend away. "
Exquisite Hagerstown Home with Deck & Gazebo!

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

10.0 out of 10, Exceptional, (5)
"Lovely property in Hagerstown. We stayed here with my 82 year old father while visiting family. Perfect accommodations! Very clean & comfortable. We had a little hiccup with our code to check in, but once Michelle saw our note, we got it fixed right away. Convenient to Main Street shops & food. We would definitely stay here again on our next trip!"
The price is AU$252
includes taxes & fees
1 Dec - 2 Dec
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Charming Home! Prime Location! Dog-Friendly!

9.6 out of 10, Exceptional, (5)
"We thoroughly enjoyed our stay. Mara was very communicative and the house was very cozy and charming. It was a delight to walk around the neighborhood and see all the beautiful historic homes. Our group of 5 adults had a great stay and we were able to bring our dog, which was great!"
The price is AU$547
includes taxes & fees
30 Nov - 1 Dec
Charming Home! Prime Location! Dog-Friendly!

Westcott Mansion with Pickleball Court & Huge Gazebo

10.0 out of 10, Exceptional, (25)
"This rental met all my expectations. We were a group of 14 ladies and the space was more than enough. Great kitchen supplies, very comfortable outside and parking. The communication was timely and informative. Thanks Richmond for a great weekend."
The price is AU$519
includes taxes & fees
8 Dec - 9 Dec
Westcott Mansion with Pickleball Court & Huge Gazebo

Quaker Hill Cottage on gated estate with fire pit & hiking trails

9.6 out of 10, Exceptional, (19)
"Thank you so much for such a lovely home to be our home base as we returned to Richmond from all over the country to celebrate our 30th reunion at Earlham College! We loved the space, the decor and the communications with our host. "
The price is AU$346
includes taxes & fees
1 Dec - 2 Dec
Quaker Hill Cottage on gated estate with fire pit & hiking trails

La Dolce Vita

2.0 out of 10, (2)
"The pictures uploaded are either very old, or doctored. Bed sheets had stains on them with black light. Cameras installed throughout the inside of the home. No running water when we arrived. We checked into a motel, and then owner tried to charge me $2000.00 for "water damage", when there was no running water and we never stayed."
The price is AU$395
includes taxes & fees
28 Nov - 29 Nov
La Dolce Vita

Recently remodeled Colonial-style home with room for the whole family!

10.0 out of 10, Exceptional, (28)
"Lovely quiet home with pleasant outdoor area "
Recently remodeled Colonial-style home with room for the whole family!

2 Bedroom Retreat near Earlham College in Richmond IN

10.0 out of 10, Exceptional, (25)
"We loved the home along with all of the amenities. If your contemplating on which house to stay in choose this one! Cindy provided so many extras! From blankets, towels, kitchen dishes to seasonings & even the basic “staples” in the refrigerator along w snacks. Very beautiful home with character . Thankyou opening your home up to us . We will return! "
2 Bedroom Retreat near Earlham College in Richmond IN

New Hagerstown Apartment - Self Check-in. Sleeps 4+

9.6 out of 10, Exceptional, (13)
"it was closed to my fathers house, only complaint i had was that the app or website wouldnt let me message the host. kept saying didnt go thru and prompted me to retry which i did 3 times with same resuts "
The price is AU$211
includes taxes & fees
8 Dec - 9 Dec
New Hagerstown Apartment - Self Check-in. Sleeps 4+

18 Acre Farm - Pickleball, Pond, Outdoor Kitchen

10.0 out of 10, Exceptional, (5)
"We were a group of 6 siblings and a couple of their spouses. We had a great time. This is close to everything in Richmond (including Galo’s, a wonderful restaurant) but when at the home you are secluded. We got lots of use of the porch swings, fire pit, outside kitchen, lake (fishing), outside dining, etc. everything was as described and the host was amazing. Kevin and Chris treated us like family. "
18 Acre Farm - Pickleball, Pond, Outdoor Kitchen

Quaint Economy Retreat w/ Patio & Spacious Yard!

9.4 out of 10, Exceptional, (6)
"This property is maintained very well and is clean. Three people stayed and there was more than enough room. The owners were very responsive and accommodating. We would recommend this property and owner. "
Quaint Economy Retreat w/ Patio & Spacious Yard!

Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!

10.0 out of 10, Exceptional, (3)
"The house was clean, quiet, well stocked and convenient to Earlham College, with a pair of pretty horses next door. A 15-minute drive to downtown Richmond on a pretty lot, out in the country."
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!

Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!

3.0 star property
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!

THE STARR LOFT- Earlham, IUEast, Historic District

9.2 out of 10, Wonderful, (20)
"This was a great place to stay. We were in town for a concert in indy and everything in indy was a fortune. We found this place a little outside of indy but not too far. The place is amazing and beautiful. The decor fits it real.well the exposed rafters i love. Its kind of a vintage feel. I told my daughter when we got there i loved the place so much im not leaving. She told me i have to because she plans on not leaving. Plenty of food and dining just a mile or two away. I dont know if ill...
THE STARR LOFT- Earlham, IUEast, Historic District

Exquisite Hagerstown Home With Deck & Gazebo!

3.0 star property
Exquisite Hagerstown Home With Deck & Gazebo!

Quaint Economy Retreat w/ Patio & Spacious Yard!

3.0 star property
Quaint Economy Retreat w/ Patio & Spacious Yard!

Close to Earlham / IU / Reid! <br>- Nice neighborhood -

9.0 out of 10, Wonderful, (6)
"What a nice little place. Everything we needed. Didn't really use the kitchen this trip since there is family in the area but looked nicely furnished. House has been nicely updated but the older home ambiance is still there. Would love to stay again if I am back in the Richmond area and not traveling with my dogs as I usually do."
Close to Earlham / IU / Reid! <br>- Nice neighborhood -
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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Other types of properties in Williamsburg you may be interested in

Comfort Suites

2.5 star property
9.4 out of 10, Exceptional, (375)
"Newer hotel with restaurants with in walking distance. Nice breakfast options."
The price is AU$155
includes taxes & fees
22 Dec - 23 Dec
Comfort Suites

Baymont by Wyndham Richmond I-70

2.5 star property
8.0 out of 10, Very good, (1042)
"Ver friendly and helpful staff. Enjoyed Richard's breakfast."
The price is AU$111
includes taxes & fees
22 Dec - 23 Dec
Baymont by Wyndham Richmond I-70

Quality Inn and Conference Center

2.5 star property
7.0 out of 10, Good, (1067)
"Clean"
The price is AU$79
includes taxes & fees
22 Dec - 23 Dec
Quality Inn and Conference Center
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental 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.

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

Boho Bungalow off Main-one block from Lovely Park: This holiday home rental outside of Williamsburg has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Williamsburg?

While exploring the area, visit family-friendly sights like Warm Glow Candle Company, or get outside and enjoy nature at Middlefork Reservoir Park. Wayne County Fairgrounds and Indiana University East are a couple of places you'll find in the wider area.

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 offer extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.