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Canterburg Holiday Rentals

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Our top choices for Canterburg holiday rentals

1. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The Queen of Winchester Three Bedroom with Upper Level Deck

2. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (14 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is NZ$326
includes taxes & fees
16 Nov - 17 Nov
Luxury tiny home farm stay on historic property with hot tub in Stephens City

3. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (47 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is NZ$374
includes taxes & fees
1 Nov - 2 Nov
Mountain View Bungalow in Front Royal

4. Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
9.4 out of 10, Exceptional, (10 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is NZ$472
includes taxes & fees
1 Nov - 2 Nov
Cozy A frame cabin in quaint Front Royal. Dog friendly

5. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
9.4 out of 10, Exceptional, (3 reviews)
"We were staying at the schoolhouse to go hiking and ride bikes. They house has been tastefully decorated. I enjoyed the quite community and the listening to the tree frogs at night. Front Royal has a few things you can enjoy such as the movie theatre, bakery and state park. I would highly recommend this propery."
United States
Suzanne J.
The price is NZ$528
includes taxes & fees
30 Nov - 1 Dec
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

6. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Front Royal
10.0 out of 10, Exceptional, (1 review)
"The gravel road to get to the properly is an adventure. The owner described it perfectly."
United States
Denise A.
The price is NZ$684
includes taxes & fees
2 Nov - 3 Nov
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

7. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
United States
Jameson D.
Rosamond nice downtown studio apt

8. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park
Front Royal
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Very quiet neighborhood good for walking"
United States
tom c.
The price is NZ$783
includes taxes & fees
2 Nov - 3 Nov
Pool Table, Fireplace & Deck near Shenandoah Park

9. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
10.0 out of 10, Exceptional, (3 reviews)
"Really wonderful cabin. Everything was very clean and the house was super cute. Amenities were great. Would stay here again!!"
United States
Andrew G.
The price is NZ$768
includes taxes & fees
2 Nov - 3 Nov
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

10. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

NEW! Greek Spa - Frisbee Golf - Stonefire Pizza
Front Royal
The price is NZ$515
includes taxes & fees
16 Nov - 17 Nov
NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

11. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is NZ$569
includes taxes & fees
9 Nov - 10 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

12. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
The price is NZ$546
includes taxes & fees
29 Nov - 30 Nov
Newly renovated Farm cottage with Mountain views

13. Chalet w/Hot Tub, Deck, Game Room & EV Charger

Chalet w/Hot Tub, Deck, Game Room & EV Charger
Stephens City
10.0 out of 10, Exceptional, (11 reviews)
"A wonderful place to relax and enjoy being with family or friends, with lots of room for the dogs to run and play!"
United States
Laura V.
The price is NZ$797
includes taxes & fees
30 Nov - 1 Dec
Chalet w/Hot Tub, Deck, Game Room & EV Charger

14. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is NZ$646
includes taxes & fees
3 Nov - 4 Nov
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

15. Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8

Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Matt is an awesome host! This place is perfect for 2 families traveling together (fully furnished upstairs & downstairs), or 1 family wanting extra space. The hot tub is an absolute must in the fall/winter for maximum relaxation. LOVED the fire table & Blackstone grill. Very nice remodeling & appliances. Cool arcade console! Could not manage to get the fireplaces to work however."
United States
Nick G.
The price is NZ$831
includes taxes & fees
4 Nov - 5 Nov
Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8

16. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is NZ$423
includes taxes & fees
30 Nov - 1 Dec
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

17. Mountain Cabin Retreat | Hot Tub & Foosball |

Mountain Cabin Retreat | Hot Tub & Foosball |
Front Royal
8.8 out of 10, Excellent, (11 reviews)
"Amazing house in an amazing place. The deck, view and sunsets are great stress reducers. Hope to visit again!"
United States
Christine T.
The price is NZ$830
includes taxes & fees
1 Dec - 2 Dec
Mountain Cabin Retreat | Hot Tub & Foosball |

18. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is NZ$507
includes taxes & fees
1 Nov - 2 Nov
Morocco Loft 2BR overlooking city walking mall

19. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is NZ$326
includes taxes & fees
1 Nov - 2 Nov
The Blue Door steps from Handley Library
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 Canterburg Hotel Reviews

Find out more about Canterburg

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Canterburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Canterburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Canterburg. Seeing all the best attractions is bound to make you fall in love with Canterburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Canterburg short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Canterburg?

Yes, there are holiday rentals close to the most popular sights in Canterburg, 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 Canterburg has to offer?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This holiday home rental outside of Canterburg is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Canterburg?

Explore the area and family-friendly sights such as Dinosaur Land, or get out into nature at a spot like Shenandoah River. Blue Ridge Shadows Golf Club and Cedar Creek Battlefield Foundation are a couple of places you'll find in the wider area.

What are holiday rentals like in Canterburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Canterburg. Holiday 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 sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.