Photo by mary mahling carns

Search Orange County Cottages

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 10 - Oct 12
In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30

Cottages in Orange County

Charming 2-bedroom cottage in lovely Madison with WiFi, AC
Exterior

Charming 2-bedroom cottage in lovely Madison with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (9)
"House was beautiful and in a nice quiet neighborhood. Beds were SUPER comfortable, I slept amazing here. Would certainly stay again! "
$334 nightly
The price is $368
Oct 8 - Oct 9
Total with taxes and fees
Charming 2-bedroom cottage in lovely Madison with WiFi, AC
Unique Cypress cottage, close to Charlottesville with mountain views.
Exterior

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (39)
"The cabin was beautiful and a perfect place for us to relax. The location was phenomenal and closely located to Shenandoah and many amazing towns to explore."
$271 nightly
The price is $310
Oct 27 - Oct 28
Total with taxes and fees
Unique Cypress cottage, close to Charlottesville with mountain views.
1802 cottage once part of Monticello and owned by Thomas Jefferson
Exterior

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (90)
"Great place"
1802 cottage once part of Monticello and owned by Thomas Jefferson
Elegant Cottage on 600 Acre Horse & Livestock Farm
Outdoor dining

Elegant Cottage on 600 Acre Horse & Livestock Farm

9.8 out of 10, Exceptional, (146)
"Quiet, picturesque and plenty of history in the area to explore. Owners seem to be very generous in allowing guests to wander the property. Enjoyed the “things to know” information that was provided. Wish we had more time to explore the property and the surrounding area. Appreciate the pet friendly accommodations. Would stay again. "
$271 nightly
The price is $291
Oct 2 - Oct 3
Total with taxes and fees
Elegant Cottage on 600 Acre Horse & Livestock Farm
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Terrace/patio

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

10.0 out of 10, Exceptional, (38)
"Thank you so much Juli - guests enjoyed a wonderful stay!!"
$236 nightly
The price is $270
Oct 26 - Oct 27
Total with taxes and fees
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Bluebird Cottage A: Near Charlottesville, Wineries: Firepit, Patio, Dogs OK
Exterior

Bluebird Cottage A: Near Charlottesville, Wineries: Firepit, Patio, Dogs OK

10.0 out of 10, Exceptional, (38)
"Love staying here. It’s always a great place to stay "
Bluebird Cottage A: Near Charlottesville, Wineries: Firepit, Patio, Dogs OK
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Exterior

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

9.0 out of 10, Wonderful, (121)
"Close to good food and attractions in the area. Monticello, Trump Winery, Downtown CVille. "
$190 nightly
The price is $210
Oct 16 - Oct 17
Total with taxes and fees
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Charming Cottage on beautiful Farm & Vineyard
Outdoor dining

Charming Cottage on beautiful Farm & Vineyard

10.0 out of 10, Exceptional, (33)
"Great stay, great place!"
Charming Cottage on beautiful Farm & Vineyard
Loveshack, a charming tiny house on a 5 acre farm
Property grounds

Loveshack, a charming tiny house on a 5 acre farm

9.6 out of 10, Exceptional, (7)
"My wife and I had a great weekend getaway. Property was great. Close to restaurants and hiking. Great hosts."
Loveshack, a charming tiny house on a 5 acre farm
Stonemont Farm Cottage in Keswick near Vineyards!
Exterior

Stonemont Farm Cottage in Keswick near Vineyards!

9.8 out of 10, Exceptional, (24)
"Clean, beautiful view, quiet! Will definitely stay again."
Stonemont Farm Cottage in Keswick near Vineyards!
Charming Eastham Guesthouse
Terrace/patio

Charming Eastham Guesthouse

2.0 star property
10.0 out of 10, Exceptional, (1)
"Cute place! Exactly as pictured. We loved our stay! Beautiful location! Take a picture of the key code to get in the door as cell service is spotty. "
$195 nightly
The price is $223
Oct 5 - Oct 6
Total with taxes and fees
Charming Eastham Guesthouse
Red Roof Retreat at Lake Anna, Waterfront w/kayaks, fire pit, grill & large deck
Exterior

Red Roof Retreat at Lake Anna, Waterfront w/kayaks, fire pit, grill & large deck

10.0 out of 10, Exceptional, (4)
"Nice, relaxing get away. "
Red Roof Retreat at Lake Anna, Waterfront w/kayaks, fire pit, grill & large deck
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
Exterior

Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors

10.0 out of 10, Exceptional, (48)
"Very peaceful and comfortable place to stay."
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
COME AND STAY WITH US FOR MEMORIES THAT WILL LAST A LIFETIME!!
Exterior

COME AND STAY WITH US FOR MEMORIES THAT WILL LAST A LIFETIME!!

9.8 out of 10, Exceptional, (70)
"We loved our stay here. If you’re looking for a private, quiet, and secluded place that is still convenient to good restaurants, wineries, shops, and historic sites, this place is for you. Our host was so helpful, and her dogs were an added bonus. We would stay here again."
COME AND STAY WITH US FOR MEMORIES THAT WILL LAST A LIFETIME!!
Bluebird Cottage B: Firepit, Patio, Games; Near Charlottesville, Wineries
Exterior

Bluebird Cottage B: Firepit, Patio, Games; Near Charlottesville, Wineries

10.0 out of 10, Exceptional, (48)
"Property very clean, comfy bed! Everything we needed for our stay. "
Bluebird Cottage B: Firepit, Patio, Games; Near Charlottesville, Wineries
Fire Pits, Creek View: Historic Virginia Farmhouse
House (3 Bedrooms) | Interior

Fire Pits, Creek View: Historic Virginia Farmhouse

3.0 star property
Fire Pits, Creek View: Historic Virginia Farmhouse
Blue Ridge Avenue Guest House
Terrace/patio

Blue Ridge Avenue Guest House

9.8 out of 10, Exceptional, (49)
"Great location, great property."
Blue Ridge Avenue Guest House
Relax at 3100 feet and enjoy the peace and tranquility
Property grounds

Relax at 3100 feet and enjoy the peace and tranquility

10.0 out of 10, Exceptional, (78)
"The views from the porch is amazing. Some of our hikes to summits had a less beautiful view. Nice place with cute decor and everything you need to cook and hang out. The mountain road up is worth the ride.We really loved our trip and stay. "
Relax at 3100 feet and enjoy the peace and tranquility
1840s Cottage close to I-95
Microwave, oven, stovetop, cookware/dishes/utensils

1840s Cottage close to I-95

9.2 out of 10, Wonderful, (18)
"Pet Friendly "
$145 nightly
The price is $166
Oct 8 - Oct 9
Total with taxes and fees
1840s Cottage close to I-95
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Exterior

Servants' Cottage on 600 Acre Working Horse/Cattle Estate

9.8 out of 10, Exceptional, (137)
"Property was very peaceful. Very much enjoyed the stay. Everyone was very friendly. "
$185 nightly
The price is $199
Oct 6 - Oct 7
Total with taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Orange County Hotel Reviews

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Good location, easy check-in. Little loud in the hallways."
Luca 2-night trip
Posted 12 hours ago
Comfort Inn & Suites

Find out more about Orange County

Find out more about Orange County

Orange County Cottages information

Number of reviews
978
Accommodation
127 Cottages
Lowest Price
$166
Highest Price
$368

Explore a world of travel with Expedia

Explore a world of travel with Expedia