Fleetwood vacation rentals

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Top-rated vacation rentals in Fleetwood

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Fleetwood

4.96 out of 5 average rating, 142 reviews

"The Cottage at Cranberry Lane"

The Cottage at Cranberry Lane is 15 minutes from Boone & 20 minutes from West Jefferson. 35 minutes to Blowing Rock and nearby hiking trails. 5 minutes from the New River for tubing, canoeing and kayaking. 10 minutes from the Blue Ridge Parkway. There are many miles of bike trails along the famous Railroad Grade Rd. along the New River. The cottage is a cozy retreat in a wooded setting off the beaten path yet convenient to major roads. Suitable for couples, solo travelers, families & pets.

Mar 14 – 21

G$25,729 GYD per night

Guest favorite

Home in Fleetwood

4.95 out of 5 average rating, 149 reviews

Charming 1930s Farmhouse near Boone/W. Jefferson!

“Worth's Place" is located in the breathtaking Appalachian Mountains of Ashe County, North Carolina. This charming 1930's farmhouse sits in the locale of a "retired" 180+ acre dairy farm and is roughly 15-20 minutes away from Boone/Jefferson. If you enjoy mountain scenery, hiking trails, or any outdoor activities, Ashe County is the place to visit! NOTE: The farmhouse only has ONE BATHROOM and it is located INSIDE BEDROOM #1 (bathroom is not accessible via any other rooms besides bedroom #1).

Jan 12 – 19

G$21,942 GYD per night

Guest favorite

Guest suite in Fleetwood

4.97 out of 5 average rating, 126 reviews

Rest, Rejuvenate & Play in the NC High Country

Designed for you to rest, rejuvenate, and to play! Located high above a peaceful valley in the heart of the North Carolina High Country. Enjoy a good nights rest, and a steamy cup of morning coffee on your private deck overlooking the stunning view. The cozy private suite is the lower level of a mountain home where the owners reside, when they are in town. You will have private access to your space, deck, and hot tub. Nearby: Blue Ridge Parkway: 8 min. Boone, Todd, & West Jefferson: 20 min.

Jul 19 – 26

G$30,729 GYD per night

Guest favorite

Cabin in Fleetwood

4.97 out of 5 average rating, 155 reviews

Hillside Hideaway - Tiny Cabin, Near New River

Nestled in the Blue Ridge Mountains, the Hillside Hideaway is a tiny cabin perfect for your mountain escape. Only minutes from Boone and West Jefferson, this location is hard to beat! Just over the hill you can enjoy miles of biking and kayaking on the New River. Take in the mountain air, listen to the nearby stream, or catch a beautiful sunrise from the spacious front porch. Come relax and unwind in our modernly decorated and peaceful hideaway while still enjoying all the comforts of home.

Feb 14 – 21

G$21,418 GYD per night

Guest favorite

Guesthouse in West Jefferson

4.98 out of 5 average rating, 132 reviews

Mountain escape great views!

Leave the world behind in your private guest house. Fully stocked kitchen, living room, bedroom with two beds and bathroom with walk in shower. Enjoy great mountain views on private deck. Downtown West Jefferson, a short 4.5 mile drive, is a vibrant small town with shops, breweries, restaurants and much more. Kayak the new river, hike Mount Jefferson, drive the Blue Ridge Parkway. Enjoy cool mountain breezes in summer, beautiful fall foliage and winter sports close by. Adventure awaits!

Dec 20 – 27

G$20,753 GYD per night

Guest favorite

Guest suite in Fleetwood

4.98 out of 5 average rating, 139 reviews

High Country Hideaway, a Private Mountain Retreat!

Private 1,400 sq ft upstairs suite with separate entrance located in a peaceful mountain setting. 20 minutes to downtown Boone and 10 minutes to West Jefferson. Perfect for your getaway! Please see a special note on COVID-19 below. We offer 2 comfy bedrooms, a private bath, smart TV with Netflix, Wifi, mini fridge, microwave, coffee maker, tea kettle, and toaster. Please note: *We do not provide breakfast* Ample parking in a quiet neighborhood that is easy to find off the highway.

Jun 21 – 28

G$23,263 GYD per night

Guest favorite

Cabin in Fleetwood

4.97 out of 5 average rating, 489 reviews

Sleeping Bear Cabin - Blue Ridge Mountains

Sleeping Bear Cabin is nestled away in a private mountain community that has it's own lake and just a two minute drive to the New River at the entrance of the community. The cabin is surrounded by forest with a main deck and an upper deck. Just recently remodeled and redecorated, we designed Sleeping Bear to be the perfect place for anyone to enjoy the mountain life. Fishing, walking, biking, hiking, tubing, kayaking, bird, butterfly, wildlife watchers and 35 -45 minutes to skiing.

Apr 1 – 8

G$30,311 GYD per night

Guest favorite

Tiny home in Fleetwood

4.94 out of 5 average rating, 323 reviews

Tiny House with GREAT VIEWS!

My place, a custom build from HGTV-featured tiny house builder Randy Jones, is on a ridge with unparalleled, 270-degree views of Grandfather Mountain, all three area ski resorts, on in to Tennessee and Virginia's Mount Rogers. We're located 20 minutes from Boone and West Jefferson, and closer than that to the Blue Ridge Parkway and New River activities like fishing and tubing. If you've considered downsizing, or you just want to give living tiny a try for a getaway, this is the place!

Sep 7 – 14

G$14,769 GYD per night

Guest favorite

Cabin in Todd

4.99 out of 5 average rating, 194 reviews

Creekside Cabin in Todd, NC!

Guests love the location & modern amenities! All 5 Stars! Fox Den at Boulder Creek is a rugged, yet refined, retreat only a short drive from Boone and West Jefferson. Its the perfect basecamp for all the adventures that await in the High Country. Styled with furnishings from West Elm and Room and Board, its a perfect pairing of Rustic and Modern with thoughtful details like throws for snuggling on the sofa and flameless candles to add that cozy feeling. Plus, an outdoor campfire area!

Nov 1 – 8

G$35,179 GYD per night

Guest favorite

Cottage in Purlear

4.98 out of 5 average rating, 230 reviews

Enchanted Mtn Cottage Escape/Farm/10 Miles to BRP

Quiet and peaceful private mountain cottage, with unique vintage decor. Sleeps 2, with a fully appointed kitchen and living area, very comfortable queen bed, bathroom with shower, new Washer/Dryer and a spacious deck, with patio table and chairs, overlooking the farm. Stream and fire pit below. Remote and private, but easily accessible to town and all the surrounding mountain areas Conveniently located near Wilkesboro (10 miles), Blue Ridge Parkway (10 miles), Boone (20 miles)

Oct 26 – Nov 2

G$21,899 GYD per night

Guest favorite

Cabin in Fleetwod

4.95 out of 5 average rating, 428 reviews

Tiny cabin - Giant view

Tiny Charm with Amazing views . Enjoy the sunsets and spectacular views of three States and the Appalachian Mountains from your front porch. Cabin sits on top of a mountain surrounded by Christmas trees and wide open spaces. It is tiny, but comfortably and decorated with all the amenities desired for a sweet getaway. (Three other tiny cabins nearby ~60 ft apart). Sorry, no pets allowed. Offenders will be fined $100. Winter months: 4WD required.

Sep 12 – 19

G$24,801 GYD per night

Guest favorite

Cabin in Fleetwod

4.95 out of 5 average rating, 437 reviews

Tiny Home, Amazing Views

This house was designed and built just for your perfect getaway. It's nestled high up on our family land with hundreds of acres of pure nature surrounding, you can see three different states, the ski slopes and a perfect sunset every single night right in front of you! The main floor has a super cozy living, dining and kitchen followed by the bathroom and bedroom with a king sized bed. The upstairs is a children's loft with 3 single beds.

Aug 14 – 21

G$25,752 GYD per night