Fairfield Vacation Rentals

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Oct 25 - Oct 26
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Oct 26 - Oct 27
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Oct 31 - Nov 2
In two weeks
Nov 7 - Nov 9

Vacation Rentals in Fairfield

2 bedrooms, free WiFi, bed sheets
Luxury cabin in the woods, 2 bedrooms plus loft
Luxury cabin in the woods, 2 bedrooms plus loft
10.0 out of 10, Exceptional, (185)
"Place was a nice in person as advertised. Would definitely stay there again!"
United States
John W.
Luxury cabin in the woods, 2 bedrooms plus loft
Property grounds
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
10.0 out of 10, Exceptional, (38)
"Everything about this stay was fantastic –– would rebook this place in a heartbeat if/when we are back in the area!"
United States
Eli S.
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (295)
"Very nice location and place to stay. The condo was a little beat up though. "
United States
Lance S.
The price is ￥16,050
￥37,250 total
includes taxes & fees
Nov 9 - Nov 10
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Property grounds
Lovely C.1890 Flat with Garden in Historic Downtown
Lovely C.1890 Flat with Garden in Historic Downtown
9.8 out of 10, Exceptional, (69)
"Great location! Great stay!"
United States
margot m.
The price is ￥25,406
￥36,415 total
includes taxes & fees
Oct 26 - Oct 27
Lovely C.1890 Flat with Garden in Historic Downtown
Miscellaneous
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
10.0 out of 10, Exceptional, (247)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
United States
Martha J.
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Sauna
Fully Loaded 8BR in Wintergreen! Sleeps 23
Fully Loaded 8BR in Wintergreen! Sleeps 23
2.0 star property
Fully Loaded 8BR in Wintergreen! Sleeps 23
Exterior
Wow! What A View!
Wow! What A View!
10.0 out of 10, Exceptional, (53)
"Property was gorgeous with amazing mountain views! Comfortable beds, beautiful kitchen and large living room for relaxing. Great location. Can’t wait to stay here again!"
United States
Timmie T.
Wow! What A View!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, (330)
"Great condo in a super convenient location, steps from the resort!! Super responsive and friendly host!"
United States
Juan A.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Exterior
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
10.0 out of 10, Exceptional, (37)
"Great property and host"
United States
Christopher B.
The price is ￥22,126
￥35,130 total
includes taxes & fees
Oct 28 - Oct 29
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Fridge, microwave, oven, stovetop
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
9.6 out of 10, Exceptional, (52)
"Great place to stay for a relaxing weekend in the mountains to escape the heat. Greatly appreciated the fully stocked kitchen! It is truly fully stocked, unlike so many rental places which only claim to be. "
United States
Ryan M.
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Property grounds
Cozy Cabin with private HOT TUB!
Cozy Cabin with private HOT TUB!
10.0 out of 10, Exceptional, (26)
"This location was a nice place to relax and enjoy family time."
United States
Melissa H.
Cozy Cabin with private HOT TUB!
Pool
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
9.6 out of 10, Exceptional, (137)
"Very clean place and very accommodating host"
United States
Jeff
The price is ￥16,815
￥38,110 total
includes taxes & fees
Nov 3 - Nov 4
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Outdoor dining
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
9.6 out of 10, Exceptional, (4)
"Beautiful view, gorgeous sunrises, well maintained"
United States
Charlotte M.
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
Dining
Rustic Mountain Retreat-Bear Paw
Rustic Mountain Retreat-Bear Paw
9.8 out of 10, Exceptional, (232)
"The river access is top notch. Great location near a bunch of hikes. A perfect, peaceful spot for a weekend. "
United States
John M.
Rustic Mountain Retreat-Bear Paw
Exterior
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
9.8 out of 10, Exceptional, (15)
"Cabin was clean and tidy. Everything i needed was there. I felt comfortable and safe. This is important because I was traveling alone. This feels like it will be my get away spot in the future. Host was polite and quick to respond"
United States
Lori M.
The price is ￥22,126
￥34,786 total
includes taxes & fees
Oct 26 - Oct 27
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Fridge, microwave, oven, stovetop
Elegant & Modern Carriage House at Twin Maple Farm
Elegant & Modern Carriage House at Twin Maple Farm
10.0 out of 10, Exceptional, (207)
"Very pleasant stay -- had everything we needed and very quiet. "
United States
Jennifer M.
The price is ￥23,651
￥34,836 total
includes taxes & fees
Nov 6 - Nov 7
Elegant & Modern Carriage House at Twin Maple Farm
Exterior
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
10.0 out of 10, Exceptional, (9)
The price is ￥15,259
￥29,212 total
includes taxes & fees
Nov 3 - Nov 4
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Property grounds
NEW! Warren’s Woods! Cozy 5-bedroom house in fantastic Wintergreen Resort
NEW! Warren’s Woods! Cozy 5-bedroom house in fantastic Wintergreen Resort
10.0 out of 10, Exceptional, (1)
"We had a fabulous stay at Warren’s Woods! The location of the house is perfectly situated within Wintergreen, a short walk or drive to hiking and the main resort facilities. We enjoyed the hot tub and wood burning fireplace. The kitchen was very well stocked and the layout of the house was great for 2 families. We’ll be back! 5 stars! "
United States
Beth K.
NEW! Warren’s Woods! Cozy 5-bedroom house in fantastic Wintergreen Resort
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen
New Build! Log Cabin with Hot Tub in Wintergreen
10.0 out of 10, Exceptional, (2)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
New Build! Log Cabin with Hot Tub in Wintergreen
Property grounds
The Modern Mountain Condo
The Modern Mountain Condo
10.0 out of 10, Exceptional, (30)
"Ideal location for skiing at Wintergreen. "
United States
Ashok G.
The price is ￥15,277
￥37,035 total
includes taxes & fees
Oct 26 - Oct 27
The Modern Mountain Condo
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 Fairfield Hotel Reviews

Comfort Inn & Suites Raphine - Lexington near I-81 and I-64

Comfort Inn & Suites Raphine - Lexington near I-81 and I-64

10/10 Excellent
"Staff was very friendly and helpful"
Gena 1-night trip
Posted 16 hours ago
Comfort Inn & Suites Raphine - Lexington near I-81 and I-64

Find out more about Fairfield

Search for holiday rentals in Fairfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Fairfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Fairfield!

Frequently asked questions

Are there vacation rentals in Fairfield?

Yes, we have vacation rentals close to popular sights in Fairfield, or you can select a more remote option if you're looking for a relaxing stay. Fairfield is known for its parks.

What are some of the best vacation rentals in Fairfield?

NEW! Warren’s Woods! Cozy 5-bedroom house in fantastic Wintergreen Resort: Visitors like this Fairfield vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Fairfield?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Fairfield stay.

What can I see and do in Fairfield?

Explore the area and family-friendly sights such as Virginia Safari Park, or get out into nature at a spot like George Washington National Forest. In the larger area, you’ll find Virginia Horse Center and Southern Virginia University.

What are vacation rentals like in Fairfield?

Vacation rentals are private accommodations you can book for several days or longer in Fairfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.