Windsor Hills Holiday Rentals

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Holiday Rentals in Windsor Hills

Private 2 bedroom bungalo
9.8 out of 10, Exceptional, (31)
"Loved our stay here! The property is very private but also in a very central location in Roanoke. We absolutely loved the heated pool and outdoor kitchen, and the interior was very cute. Laura gave us complete privacy but was responsive and helpful to our questions. Would definitely stay again if we end up in Roanoke!"
Private 2 bedroom bungalo
The Lofts at Downtown Salem
3.5 star property
9.6 out of 10, Exceptional, (189)
"Recommend this loft."
The price is NZ$266
per night
9 Jun - 10 Jun
The Lofts at Downtown Salem
Modern Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit 🔥
10.0 out of 10, Exceptional, (26)
"We've stayed at many VRBOs and this adorable cottage ranks very high on our list! It was the cleanest place we've ever stayed and we really appreciated all of the extra towels and cozy blankets. The hot tub and fire pit were fun evening activities, and the smart tvs came loaded with many of our favorite programs. The appliances were brand new and the kitchen had everything we needed, including an electric tea kettle. The backyard view was fantastic, and we also enjoyed sitting on the front porch...
The price is NZ$366
per night
24 Jun - 25 Jun
Modern Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit 🔥
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Briarcliff - 3000 sq ft waterfront home w/ private dock, 2 kitchens & pool table
9.8 out of 10, Exceptional, (33)
"This was a last minute booking. One snafu with Vacasa with them not being able to verify my ID via DL but with a quick phone call that was corrected. The home itself is nice and has plenty of space and amenities. The decibel reader is a little off-putting but I understand with VA laws being the way they are. Overall, it was a nice stay."
Briarcliff - 3000 sq ft waterfront home w/ private dock, 2 kitchens & pool table
The West End Flats
4.5 star property
10.0 out of 10, Exceptional, (2)
The price is NZ$183
per night
6 Jun - 7 Jun
The West End Flats
Studio w/pool & hot tub -only minutes to Triple Crown hiking trails
10.0 out of 10, Exceptional, (14)
"Lovely clean and well equipped! Nice touches like bottled water and snacks available."
The price is NZ$174
per night
8 Jun - 9 Jun
Studio w/pool & hot tub -only minutes to Triple Crown hiking trails
2.5 wooded acres on quiet deep water cove - create great vacation memories.
9.4 out of 10, Exceptional, (124)
"We have stayed here several times on spring break to celebrate our daughter’s birthday. Is the perfect dock for hanging out with friends and family, and the teens love the pool table and their own space downstairs, the adults love the big table upstairs to play cards. Owners have updated the main bathroom and the basement since we stayed there last, which is really nice."
2.5 wooded acres on quiet deep water cove - create great vacation memories.
Cute cottage feel apartment, dog friendly
6.0 out of 10, (2)
"The property was inaccessible. There was no key in the lockbox and the space was clearly not livable. I was unable to stay there. Still haven't received a refund from VRBO."
Cute cottage feel apartment, dog friendly
Historic Rooftop Loft Apartment Downtown
10.0 out of 10, Exceptional, (50)
"We really enjoyed our stay here. Beautiful place and great location. Easy communication with the host. We would definitely stay here again."
The price is NZ$341
per night
6 Jun - 7 Jun
Historic Rooftop Loft Apartment Downtown
Real Log Cabin w/ Trout Pond close to Mcaffee Knob, Dragons tooth, Tinker Cliffs
9.8 out of 10, Exceptional, (17)
"The property is beautiful and peaceful. The log cabin built by the owner is gorgeous and equipped with the essentials needed. I would love to stay here again for a longer period of time."
The price is NZ$515
per night
4 Jun - 5 Jun
Real Log Cabin w/ Trout Pond close to Mcaffee Knob, Dragons tooth, Tinker Cliffs
A home away from home close to hiking trails! Sleeps 6! Pet friendly!
9.6 out of 10, Exceptional, (5)
"We hosted our 2022 family Thanksgiving at this home, and we were so happy with our stay and the location! Missy (the host) made sure everything was perfect for our stay and we had excellent communication during our stay - she is super responsive. Beds were very comfortable, ample linens, kitchen supplies, and sitting room for our party. We loved sitting around the firepit in the backyard and the front porch to watch the sunsets. It was truly a wonderful country escape. Thanks for being a...
The price is NZ$517
per night
9 Jun - 10 Jun
A home away from home close to hiking trails! Sleeps 6! Pet friendly!
Cute • Modern • Self check-in • Close to DownTown • Dog Friendly!
9.4 out of 10, Exceptional, (3)
"House is clean and perfect for us. Would recommend 10/10"
The price is NZ$397
per night
11 Jun - 12 Jun
Cute • Modern • Self check-in • Close to DownTown • Dog Friendly!
Downtown Roanoke
7.2 out of 10, Good, (5)
"We came in for the marathon and just needed a place to stay.it was walking distance to everywhere we wanted to go. Furniture was kinda cheap and the pool table was useless. But excellent for what we needed."
Downtown Roanoke
Mountain Creek Lodge located within 20 minutes of Virginia Tech
9.4 out of 10, Exceptional, (11)
"I was looking for a place to getaway for a couple of days and disconnect from all of my distractions, and this cabin offered everything that I was looking for in my get away. The location is great, not too close but not too far from Blacksburg and convenient to good hiking trails in the area."
The price is NZ$654
per night
4 Jun - 5 Jun
Mountain Creek Lodge located within 20 minutes of Virginia Tech
Relax at Dock Holiday on Smith Mountain Lake
6.0 out of 10, (2)
"This was a trip our family really needed. The house was big and had room for everything we wanted to do. The guys just did not catch the fish they thought they would catch. The decks were great. I host was amazing, she responded quickly when we needed her."
Relax at Dock Holiday on Smith Mountain Lake
1 Special Place - Waterfront home with private dock, lake views, & washer/dryer
9.6 out of 10, Exceptional, (44)
""I recently had the pleasure of staying at this charming vacation rental cabin by the lake, and it was an absolute gem. The cabin itself is not only beautifully designed but also impeccably maintained. The large bedrooms were a pleasant surprise, providing ample space for everyone in our group. One of the highlights of our stay was the two decks, which allowed us to soak in the tranquil surroundings from different vantage points. The boating dock with its picturesque view was a favorite spot...
1 Special Place - Waterfront home with private dock, lake views, & washer/dryer
The Virginia Country Cottage: GREAT Location/Pet Friendly, 30 Acres, close I81
10.0 out of 10, Exceptional, (113)
"I truly enjoyed staying at this property. My friend and I were on a research trip and spent a lot of time on the front porch working. WiFi was very strong and the home was fully furnished with everything we needed. We were even invited to pick fresh strawberries in the garden! We both really enjoyed ourselves and agreed when we have to do one more trip in VA we’ll be staying here again."
The Virginia Country Cottage: GREAT Location/Pet Friendly, 30 Acres, close I81
Simple but functional home in a diverse neighborhood
Simple but functional home in a diverse neighborhood
Huge Dock, Big Water, >200 Mb/s WiFi, Canoe, 3 King, Queen, and Bunks for Kids
10.0 out of 10, Exceptional, (97)
"Great space for the weekend"
Huge Dock, Big Water, >200 Mb/s WiFi, Canoe, 3 King, Queen, and Bunks for Kids
Goodview Home w/ Decks & Direct Lake Access!
9.4 out of 10, Exceptional, (8)
"Had a great time this winter! Peaceful location, plenty of room, and no issues!"
Goodview Home w/ Decks & Direct Lake Access!
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See all available properties in Windsor Hills
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.

Other types of properties in Windsor Hills you may be interested in

Private 2 bedroom bungalo
9.8 out of 10, Exceptional, (31)
"Loved our stay here! The property is very private but also in a very central location in Roanoke. We absolutely loved the heated pool and outdoor kitchen, and the interior was very cute. Laura gave us complete privacy but was responsive and helpful to our questions. Would definitely stay again if we end up in Roanoke!"
Private 2 bedroom bungalo
Country Inn & Suites by Radisson, Roanoke, VA
3.0 star property
9.0 out of 10, Wonderful, (1357)
"This was my second stay at this hotel. The rate was really low.The rooms are large; however parking is limited. That night the grass was mowed which made it difficult to fall asleep. My first stay here was great. It's under new management."
The price is NZ$185
per night
23 Jun - 24 Jun
Country Inn & Suites by Radisson, Roanoke, VA
The Liberty Trust
4.0 star property
9.2 out of 10, Wonderful, (689)
"Really great experience: easy check in and very accommodating "
The price is NZ$315
per night
16 Jun - 17 Jun
The Liberty Trust
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.

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 Windsor Hills 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 Windsor Hills. 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 Windsor Hills. Seeing all the best attractions is bound to make you fall in love with Windsor Hills. 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 Windsor Hills short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Windsor Hills?

Yes, there are holiday rentals close to the most popular sights in Windsor Hills, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in Windsor Hills?

Explore the area and family-friendly sights such as Mill Mountain Zoo, or get out into nature at a spot like River's Edge Sports Complex. Tanglewood Mall and Salem Civic Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Windsor Hills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor Hills. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family gatherings.

Recent reviews of Windsor Hills properties
Expedia verified reviews