Holiday rentals in Woodstock

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Top-rated holiday rentals in Woodstock

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Guest favourite

Guest house in Mount Jackson

4.98 out of 5 average rating, 381 reviews

The Hay Loft

The Hay Loft sits in the middle of 43 beautiful acres, overlooking our working hay farm with stunning views of the Shenandoah Mountains. We are conveniently located near restaurants, vineyards, antiquing, battlefields, golf resorts, ski resorts and caverns. Spacious rustic/luxe suite w/gas fireplace; king bed and bathroom with tiled shower, Keurig coffee maker, microwave, toaster oven, small refrigerator, no freezer, dishes and and outdoor gas grill and indoor gas fireplace. Outdoor firepit.

3–10 Jun

£123 per night

Guest favourite

Tiny home in Quicksburg

4.99 out of 5 average rating, 176 reviews

Finn's Frolic-The place- relax, stay, or explore!

Finn's Frolic is our charming, new country tiny home. Less than 2 hours DC, Charlottesville. Beautiful farm, mountain views, deck, fire pit, charcoal grill, much more. Landscaping is in the works ! Kitchen is fully equipped, vintage & new dinner wear. Living room has an electric fireplace, huge picture window, comfy love seat. The bedroom is up traditional stairs: loft bedroom, 7 foot sloped ceiling. Great place to relax, base for visits to local wineries, attractions! Perfectly imperfect!

10–17 Aug

£85 per night

Guest favourite

Home in Edinburg

4.98 out of 5 average rating, 351 reviews

Jay Birds Nest - Pet Friendly

Welcome to Jay Birds nest, located in the historic town of Edinburg, Virginia. Just 1.5 miles from I-81. Fully equipped with all the comforts of home and gorgeous mountain views. Enjoy having the entire house to yourself with sleeping for 6 with one queen bedroom and 2 double bedrooms and one full bath. Plenty of parking with room for two cars, one under a car port. Have your morning coffee in the relaxing sunroom or in the outdoor seating area. Just a quick walk away from the Shenandoah River.

5–12 Feb

£96 per night

Guest favourite

Guest suite in Woodstock

4.96 out of 5 average rating, 302 reviews

Mountain View🌄 Modern Basement Suite*King Bed*Wifi

Amazing Mountain Views from this modern Scandinavian inspired guest suite nestled in the heart of the Shenandoah Valley!! Close to hiking, wineries, the river! Enjoy a cup of coffee on the patio and watch the sun rise over the mountains, unwind and watch a movie on the app connected flatscreen TV, refresh in the oversized shower with multiple heads including a rainfall feature. This two bedroom suite has its own entrance, private covered patio with mountain views and parking spot steps away.

9–16 Aug

£210 per night

Guest favourite

Home in Edinburg

4.99 out of 5 average rating, 335 reviews

The Burrow ~ Our guest reviews say it all!

Indulge in a serene retreat at this charming countryside residence, perfect for a delightful getaway or a quick overnight stay. Just a 4-minute drive with two easy turns from I-81, this cozy home promises tranquility and relaxation. Begin your day on the inviting porch, soaking in the sunrise, setting the tone for a peaceful escape. Explore attractions such as hiking trails, enchanting caverns, or indulge in the local offerings of nearby wineries. A short stroll reveals Dee and Kenn's home.

8–15 Jan

£124 per night

Guest favourite

Home in Edinburg

4.96 out of 5 average rating, 149 reviews

Charming, Parkview Cottage, King bed, 1 mi to I-81

Welcome to Parkview Cottage you will love this Cozy, 1940's home for a quiet fun getaway or quick overnight stay located in small rural town with an easy 1 mile from I-81. Enjoy quiet mornings on the porch watching the sunrise and a few neighbors stroll by out on morning walks and then venture off for the neighboring park, a hike, canoe trip, trip to the caverns or wineries close by. Enjoy the sunset from the sunroom over Edinburg Park. Park under the oversized "2 car" carport.

22–29 Aug

£135 per night

Guest favourite

Guest house in New Market

4.99 out of 5 average rating, 175 reviews

Stay in a piece of history! Private Entire Cottage

Built in 1797, this cottage sits next to the historic William Rupp House, and is #17 on the self-guided walking tour! Although you are staying in a piece of history, you still get the privacy you need to comfortably explore all Shenandoah Valley has to offer. 19.6 miles away from JMU, 5.2 miles away from Endless Caverns, right off Interstate 81, and within walking distance of local stores, coffee shops, and restaurants... buckle in for a load of fun with this convenient location.

29 Sept – 6 Oct

£91 per night

Guest favourite

Guest house in Maurertown

4.97 out of 5 average rating, 374 reviews

Guest Suite at Little Ridge

Enjoy your own private suite on our newly established farmstay and taphouse, out in the beautiful Shenandoah Valley! Plenty of space to hang out on the farm with some beautiful views. The tap room and cafe' are open Friday 5-9pm, Sat 12-9pm & Sun 12-6pm. We are just minutes from historic downtown Woodstock. The Valley is know for her spectacular hiking trails and caverns. After a long day exploring, you will be sure to enjoy a relaxing and entertaining evening with us.

31 Aug – 7 Sept

£113 per night

Guest favourite

Cabin in Lost River

4.95 out of 5 average rating, 111 reviews

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

20–27 Dec

£93 per night

Guest favourite

Cottage in Woodstock

4.98 out of 5 average rating, 176 reviews

Cottage on Boxwood Lane

Welcome to the Cottage on Boxwood Lane! Our cozy cottage makes you feel disconnected from the world, while sitting in the middle of quaint Woodstock, Virginia in the heart of the Shenandoah Valley. This 420 sq ft cottage with ample parking features a small bedroom with one queen bed, one bathroom with a shower, living room, and a kitchenette. The kitchenette has a full-sized fridge, induction cooktop, toaster oven, microwave, coffee maker, and sink.

12–19 Sept

£87 per night

Guest favourite

Guest suite in Woodstock

4.89 out of 5 average rating, 233 reviews

Easy, Private and Peaceful, 2 minutes from I-81

Relax in a quiet private suite right off I-81. It's clean and sanitized following CDC guidelines. A self check-in touch pad lock for ease of entry and exit. Located 2 minutes from historic Woodstock, minutes from wineries, breweries, the Shenandoah River, State and National Forests. Private entrance, yard and parking. Comfortable and cozy queen sized bed, kitchenette, coffee maker, microwave, refrigerator, bathroom and shower with WiFi

28 Jun – 5 Jul

£57 per night

Guest favourite

Guest suite in Maurertown

4.85 out of 5 average rating, 186 reviews

Studio along i81: Near Wine, Beer, Hiking & Nature

Newly renovated detached studio guest-suite located in the beautiful Shenandoah County with country feels and easy access to I81. It features a butcher block bar for eating/working, a queen size bed, tv with Netflix along with Chromecast so you can cast your favorite shows from your phone/laptop, and during the summer you'll have the quietest and smart ac unit on the market. It has a shared driveway with the host's primary residence.

27 May – 3 Jun

£62 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Woodstock holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Woodstock's top sights

Cracker Barrel Old Country Store15 locals recommend

Walmart Supercenter14 locals recommend

Woodstock Brewhouse81 locals recommend

Las Trancas17 locals recommend

Woodstock Cafe61 locals recommend

Seven Bends State Park30 locals recommend

Other great holiday rentals in Woodstock

Guest favourite

Cabin in Lost City

4.97 out of 5 average rating, 247 reviews

High View Hideaway - A Cozy Lost River Cabin

15–22 Jun

£104 per night

Guest favourite

Tiny home in Linville

4.99 out of 5 average rating, 600 reviews

The spring house at Thistle Hollow

12–19 Aug

£105 per night

Guest favourite

Home in Woodstock

4.96 out of 5 average rating, 105 reviews

The Beckford House in Historic Woodstock

3–10 Aug

£252 per night

Guest favourite

Guest house in Woodstock

4.95 out of 5 average rating, 87 reviews

Cozy cottage nestled on 8 acres with mountain view

19–26 May

£82 per night

Guest favourite

Home in Woodstock

5.0 out of 5 average rating, 72 reviews

Historic Charm Meets Modern Luxury @ On Cloud Wine

17–24 Sept

£161 per night

Superhost

Home in Woodstock

4.78 out of 5 average rating, 18 reviews

Modernized historic farm house.

16–23 Sept

£127 per night

Guest favourite

Flat in Woodstock

4.91 out of 5 average rating, 11 reviews

The Roost at the Hen House

24–31 Oct

£124 per night

Guest favourite

Cabin in Woodstock

5.0 out of 5 average rating, 33 reviews

The Bird's Nest - Cabin by the River

26 Aug – 2 Sept

£203 per night

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Quick stats about holiday rentals in Woodstock

Total rentals	20 properties
Popular amenities	Gym, BBQ grill and Laptop-friendly workspace
Wifi availability	20 properties include access to wifi
Family-friendly rentals	10 properties are a good fit for families
Total number of reviews	2K reviews
Nightly prices starting at	£48 before taxes and fees

Holiday rentals in Woodstock

Top-rated holiday rentals in Woodstock

Guest house in Mount Jackson

Tiny home in Quicksburg

Home in Edinburg

Guest suite in Woodstock

Home in Edinburg

Home in Edinburg

Guest house in New Market

Guest house in Maurertown

Cabin in Lost River

Cottage in Woodstock

Guest suite in Woodstock

Guest suite in Maurertown

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Woodstock holiday rentals

Stay near Woodstock's top sights

Other great holiday rentals in Woodstock

Cabin in Lost City

Tiny home in Linville

Home in Woodstock

Guest house in Woodstock

Home in Woodstock

Home in Woodstock

Flat in Woodstock

Cabin in Woodstock

Quick stats about holiday rentals in Woodstock

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore