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Top Holiday Rentals in Orange

8br, bed rms Anna lakefront, 3 levels, 6.5k sf, pool completion 7/2025, 16 pers.

8br, bed rms Anna lakefront, 3 levels, 6.5k sf, pool completion 7/2025, 16 pers.

Lakeside retreat with a firepit, dock, sprawling deck, pool table - dog friendly

9.2 out of 10, Wonderful, (15)
"We spent a week at this house and enjoyed the location and accommodations. (Family with 5 adults for the stay.)"
Lakeside retreat with a firepit, dock, sprawling deck, pool table - dog friendly

Lakefront Cabin: Sunset View+Jetted tub+ Tesla Charger

9.6 out of 10, Exceptional, (19)
"Our family has the best time! The host made for a very comfortable and peaceful stay! The accommodations worked very well for a family. The area was very quiet and serene."
Lakefront Cabin: Sunset View+Jetted tub+ Tesla Charger

Boardwalk Hotel on Lake Anna by Kasa

4.0 star property
9.2 out of 10, Wonderful, (33)
"Very clean and beautiful place "
The price is £103
includes taxes & fees
8 Jul - 9 Jul
Boardwalk Hotel on Lake Anna by Kasa

Postcard Cabins Shenandoah

2.0 star property
10.0 out of 10, Exceptional, (15)
"We really enjoyed our stay. Real close to Shenandoah National Park. "
The price is £178
includes taxes & fees
7 Jul - 8 Jul
Postcard Cabins Shenandoah

Wilderness Presidential Resort

3.0 star property
9.0 out of 10, Wonderful, (59)
"My second time back with the kids and we still haven’t experience all of the activities which is exciting for me because we have a reason to keep coming back! The place is awesome and relaxing!"
The price is £149
includes taxes & fees
7 Jul - 8 Jul
Wilderness Presidential Resort

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

9.0 out of 10, Wonderful, (111)
"Owners were easy to reach and very kind!! Place was clean and easy to locate. Everything about it rocked!"
The price is £152
includes taxes & fees
7 Jul - 8 Jul
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

NEW Serene Lakefront Lake Anna, Beach, Dock, Pool

10.0 out of 10, Exceptional, (3)
"Stunning views, comfortable accommodations, and a sense of peace and privacy"
NEW Serene Lakefront Lake Anna, Beach, Dock, Pool

Lakefront home with private hot tub, dock, grill, game room, lake views & kayaks

8.8 out of 10, Excellent, (21)
"My family and my sister's family met up here for a weekend trip. The house is beautiful and spacious. Upon arrival, the house was spotless and had everything we needed. The weather kept us in, so we can't speak too much on the outside. What we did see we loved. We will definitely be back!"
Lakefront home with private hot tub, dock, grill, game room, lake views & kayaks

Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries.

10.0 out of 10, Exceptional, (31)
"We had a beautiful stay and very secluded. We would love to come back. "
Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries.

Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing

9.0 out of 10, Wonderful, (142)
"Spent 4 days here with my fiancé and two friends , and we absolutely loved it, it was so relaxing and refreshing , the property is gorgeous Only negatives i have to say , if youre bad at following directions (which i was given) you end up on a very hard to pass road and will likely get stuck if you dont know what youre doing .. if you follow the owner directions properly you get a very easily passable road (like i said , my fault not theres but just for anyone in the future that makes the same...
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing

Breathtaking ICONIC Lake Anna Waterfront Property

9.8 out of 10, Exceptional, (20)
"Impressive property in a great location"
Breathtaking ICONIC Lake Anna Waterfront Property

Beautiful Waterfront Home On Lake Anna

10.0 out of 10, Exceptional, (123)
"This is our third time renting this property and we will continue to return annually if we can. Property has what we need in a quiet, picturesque location!"
Beautiful Waterfront Home On Lake Anna

Lakefront home with dock, washer/dryer, firepit & AC - dog-friendly

8.6 out of 10, Excellent, (22)
"This was a great place for kids, pets and family with plenty of on site entertainment!"
Lakefront home with dock, washer/dryer, firepit & AC - dog-friendly

NEW Sunrise Point Lakefront Lake Anna, Beach, Dock

10.0 out of 10, Exceptional, (3)
"We had a great time staying for a long weekend at the Sunrise Point property with our family. The house is beautiful and the location is very convenient. The land is gorgeous and perfect for entertaining. Our kids also loved to play at the privet sand beach. We are already planning our next Lake trip! "
NEW Sunrise Point Lakefront Lake Anna, Beach, Dock

Lakeview Retreat!

9.8 out of 10, Exceptional, (9)
Lakeview Retreat!

Luxurious lakefront cabin with hot tub, game room, & washer/dryer- dog friendly

9.0 out of 10, Wonderful, (51)
"Beautiful home in an awesome location. Looking forward to returning soon. "
Luxurious lakefront cabin with hot tub, game room, & washer/dryer- dog friendly

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (78)
"We absolutely loved our stay here! Absolutely beautiful property inside and out, perfect cozy spot, caught the snow which was beautiful! Only 15 minutes from town. We will definitely be back, and we loved the Alley Light suggestion from the owner which was incredible! All around it was a perfect stay, thank you!"
1802 cottage once part of Monticello and owned by Thomas Jefferson

The White Elephant Inn Getaway w/ Pool & Hot Tub!

9.8 out of 10, Exceptional, (68)
"Enjoyed our stay!"
The White Elephant Inn Getaway w/ Pool & Hot Tub!

Welcome to Gold Cove- Luxury Lake Front Home! 8,000 Sq Ft, Sleeps 23, 7 bd/7bth

10.0 out of 10, Exceptional, (69)
"This was the best house my friends, family and I have stayed at. We enjoyed how spacious the house was. A great place to stay. We will be coming every year!"
Welcome to Gold Cove- Luxury Lake Front Home! 8,000 Sq Ft, Sleeps 23, 7 bd/7bth
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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Frequently asked questions

Are there holiday rentals in Orange?

Yes, there are holiday rentals close to the most popular sights in Orange, or you can select a more secluded option if you're looking for a relaxing stay. Orange is known for its wineries and museums. Make sure you have time to check out the cafés and art during your trip.

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

Lakeside retreat with a firepit, dock, sprawling deck, pool table - dog friendly: This highly rated holiday home rental in Orange is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Orange?

Expedia has 39 holiday rentals for your stay in Orange.

What can I see and do in Orange?

Enjoy the outdoors at Rapidan River and Lake Anna, or simply take in cultural attractions like James Madison Museum and The Arts Center in Orange. Other places in town to visit include James Madison's Montpelier and St. Thomas Episcopal Church.

What are holiday rentals like in Orange?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Orange. Holiday rentals offer extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the excitement and 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 option for small groups.