An ancient stone archway with intricate carvings and columns, surrounded by trees and a clear blue sky.

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Orange vacation homes

A house with a brick chimney, a small window, and a wooden deck.

1. Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.
Orange
9.8 out of 10, Exceptional, (45 reviews)
"The stay was great. Very close to all the nearby attractions and 30 minutes to skyline drive"
United States
vishal k.
The price is CA $154
CA $234 total
includes taxes & fees
Oct 12 - Oct 13
Newly renovated entire guest suite in Orange County.
A living room with a fireplace, a chandelier, and a sofa.

2. The Pembroke Room in the historic Holladay House

The Pembroke Room in the historic Holladay House
Orange
9.4 out of 10, Exceptional, (3 reviews)
"The property is in the perfect location for a visit to Montpelier! Great restaurants and events are nearby. Very cozy! Great host! Expect what you would expect from a historic home. We will return."
United States
Robert
The price is CA $277
CA $409 total
includes taxes & fees
Oct 7 - Oct 8
The Pembroke Room in the historic Holladay House
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

3. Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Gordonsville
9.8 out of 10, Exceptional, (46 reviews)
"Beautiful property and family friendly."
United States
Tracy
The price is CA $228
CA $275 total
includes taxes & fees
Oct 5 - Oct 6
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
A living room with a dark-colored sofa, a glass coffee table, a floor lamp, and a TV mounted on the wall.

4. Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Gordonsville
9.4 out of 10, Exceptional, (39 reviews)
"Beautiful place"
United States
Berhan S.
The price is CA $313
CA $382 total
includes taxes & fees
Oct 5 - Oct 6
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
A two-story house with a porch, a front door, and a small garden with a pumpkin.

5. Charming 3-Bed Cottage on Main Street in Historic Gordonsville

Charming 3-Bed Cottage on Main Street in Historic Gordonsville
Gordonsville
10.0 out of 10, Exceptional, (18 reviews)
"This was the cutest house! Our favorite of our weeklong roadtrip. Perfect for our 6 adults. Close to town, which was adorable also. Would love to come back and stay again!"
United States
Cheryl G.
The price is CA $317
CA $551 total
includes taxes & fees
Oct 12 - Oct 13
Charming 3-Bed Cottage on Main Street in Historic Gordonsville
An outdoor patio area with two wicker chairs and a small table, surrounded by a stone wall and a white fence.

6. “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Gordonsville
10.0 out of 10, Exceptional, (38 reviews)
"Tracy was very welcoming and friendly. The accommodation was great."
United States
Linda N.
The price is CA $319
CA $456 total
includes taxes & fees
Oct 8 - Oct 9
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

7. Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Great place - clean and very easy parking. The bed was comfortable too!"
United States
Tracy
The price is CA $192
CA $353 total
includes taxes & fees
Oct 7 - Oct 8
Historic Madison Eagle Inn
A living room with a stone fireplace, black leather sofa, and a flat-screen TV mounted on the wall.

8. Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm

Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Gordonsville
9.6 out of 10, Exceptional, (35 reviews)
"The home was great, lots of space and sleeping areas. The farm itself was amazing. Would definitely stay again. Having a golf cart was a so fun."
United States
B S.
The price is CA $569
CA $694 total
includes taxes & fees
Oct 5 - Oct 6
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
A modern kitchen with wooden cabinets, a dining area with stools, a flat-screen TV mounted on the wall, and a cozy seating area with a patterned rug.

9. The Ranch at Wine Country - Complimentary Bottle!

The Ranch at Wine Country - Complimentary Bottle!
Gordonsville
10.0 out of 10, Exceptional, (52 reviews)
"The absolute cleanest place I've ever stayed. Just a clean smell when arriving. My whole family there for skydiving for only one night Very pet friendly and close attention to every detail. Bad storm resulting in losing power but host was very responsive and problem resolved. Great parking and decor. 10 out of 10"
United States
Irma S.
The price is CA $377
CA $643 total
includes taxes & fees
Oct 5 - Oct 6
The Ranch at Wine Country - Complimentary Bottle!
A geodesic dome structure with a wooden deck and two Adirondack chairs.

10. Private luxury dome with hot tub & fire pit.

Private luxury dome with hot tub & fire pit.
Unionville
The price is CA $366
CA $595 total
includes taxes & fees
Oct 13 - Oct 14
Private luxury dome with hot tub & fire pit.
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

11. Charming 4-bedroom house in Madison centrally located!

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (3 reviews)
"Our stay was excellent. The host was responsive to every need. The house was beautiful. The view from the front window is beautiful!! The bathtub and shower in the main bathroom is luxurious!! We would be willing to stay there again."
United States
Lori K.
The price is CA $311
CA $628 total
includes taxes & fees
Oct 8 - Oct 9
Charming 4-bedroom house in Madison centrally located!
A two-story house with a stone facade, a front porch, and a well-maintained lawn.

12. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (30 reviews)
"The property is perfect for a weekend getaway for a couple of a small family with kids. I really enjoyed my stay and would recommend it."
United States
Ronald
The price is CA $178
CA $321 total
includes taxes & fees
Oct 7 - Oct 8
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Living area

13. 5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more

5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more
Louisa
10.0 out of 10, Exceptional, (30 reviews)
"Had my cousin's bachelor party here. Great quiet location"
United States
David D.
The price is CA $356
CA $1,005 total
includes taxes & fees
Oct 4 - Oct 5
5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more
Exterior

14. Pine and Vine

Pine and Vine
2.0 star property
Gordonsville
The price is CA $462
CA $1,118 total
includes taxes & fees
Oct 27 - Oct 28
Pine and Vine
A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a cat sitting by the counter.

15. Charming 3-bdrm house in Ruckersville offering great location for your vacation

Charming 3-bdrm house in Ruckersville offering great location for your vacation
Ruckersville
10.0 out of 10, Exceptional, (16 reviews)
"Nice home, we enjoyed our stay. "
United States
Carol T.
The price is CA $305
CA $667 total
includes taxes & fees
Oct 4 - Oct 5
Charming 3-bdrm house in Ruckersville offering great location for your vacation
A modern kitchen with a central island, bar stools, and pendant lighting.

16. Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Etlan
10.0 out of 10, Exceptional, (31 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is CA $178
CA $279 total
includes taxes & fees
Oct 6 - Oct 7
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A spacious living area with wooden beams, a ceiling fan, a fireplace, and a large window overlooking a deck.

17. Beautiful and Private 6000 sqft waterfront home with private dock and hot tub!

Beautiful and Private 6000 sqft waterfront home with private dock and hot tub!
Mineral
10.0 out of 10, Exceptional, (8 reviews)
"We did a team retreat here, and it was a perfect spot! The house has plenty of room for people to spread out, the kitchen has just about everything you'd ever need, and the property is beautiful!"
United States
Evangeline H.
The price is CA $662
CA $1,740 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful and Private 6000 sqft waterfront home with private dock and hot tub!
A river with a sandy bank, surrounded by trees and a building on the right.

18. Beavers Bungalow-Hot-tub/WIFI

Beavers Bungalow-Hot-tub/WIFI
Mineral
9.0 out of 10, Wonderful, (29 reviews)
"The bungalow was so nice and peaceful for a quick getaway for me and my husband!! "
United States
Nicole D.
The price is CA $154
CA $494 total
includes taxes & fees
Oct 8 - Oct 9
Beavers Bungalow-Hot-tub/WIFI
A spacious kitchen with modern appliances, a dining area with a large table, and a cozy living area with a sofa and coffee table.

19. Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Madison
8.0 out of 10, Very good, (1 review)
"Positive Highlights: quiet location still close to Skyline Drive, amenities, fresh interior recently modernized, love for details (charging cables, coffee bar, etc)"
United States
Birgit W.
The price is CA $334
CA $659 total
includes taxes & fees
Oct 7 - Oct 8
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A four-poster bed with a white bedspread and pillows, a small bedside table with a lamp, a large mirror, and a window with curtains.

20. Pine and Vine: 8 Acres + Winery & Family Retreat

Pine and Vine: 8 Acres + Winery & Family Retreat
Gordonsville
10.0 out of 10, Exceptional, (1 review)
"Spectacular escape! Excellent place to relax and unwind!"
United States
TREY D.
The price is CA $462
CA $1,278 total
includes taxes & fees
Oct 27 - Oct 28
Pine and Vine: 8 Acres + Winery & Family Retreat
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 Orange Hotel Reviews

Keswick Hall

Keswick Hall

10/10 Excellent
"Absolutely beautiful property with gorgeous rooms and amenities. Good not have picked a better spot to spend our anniversary."
Maria 1-night trip
Posted 11 hours ago
Keswick Hall

Find out more about Orange

Orange Vacation Homes information

Number of reviews
391
Accommodation
648 Vacation Homes
Lowest Price
CA $234
Highest Price
CA $1,740

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