Fairfield Holiday Rentals

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Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Fairfield holiday rentals

Dining
Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge

Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge

Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge
2.0 star property
Fairfield
10.0 out of 10, Exceptional, (10)
"We had a great little break from the hustle and bustle of life. We are locals and it was nice to just get away for a few days"
United States
Don P.
The price is HK$915
HK$3,968 total
includes taxes & fees
12 Jan - 13 Jan 2026
Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge
Terrace/patio
Love Ridge Mountain Lodging

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Montebello
10.0 out of 10, Exceptional, (14)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is HK$1,005
HK$1,595 total
includes taxes & fees
28 Jan - 29 Jan 2026
Love Ridge Mountain Lodging
Property grounds
Whimsical Creekside Cabin

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (42)
"Private cabin, super clean and neat. Nature was beautiful. Love the creek next to it! "
United States
Katherine V.
The price is HK$602
HK$1,500 total
includes taxes & fees
5 Jan - 6 Jan 2026
Whimsical Creekside Cabin
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

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Buena Vista
9.6 out of 10, Exceptional, (15)
"Very nice and clean property in a quiet neighborhood. Host communicated well and left many amenities for us. Loved our stay!"
United States
Tina F.
The price is HK$777
HK$1,480 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Fridge, microwave, oven, dishwasher
Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
2.0 star property
Roseland
8.4 out of 10, Very good, (9)
"I contacted the owners to see if my family and I could check in earlier and they were about to accommodate for us. The home was clean, spacious, and had everything we needed for our stay."
United States
Sa'Mone M.
The price is HK$894
HK$2,270 total
includes taxes & fees
5 Jan - 6 Jan 2026
Bluebird Cottage: Near 151 + Appalachian Trail
Exterior
The Firefly Springhouse

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (45)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
The price is HK$644
HK$890 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Firefly Springhouse
Fridge, microwave, oven, stovetop
Simple & spacious 1-bedroom basement living in Lexington. Close to W&L and VMI

Simple & spacious 1-bedroom basement living in Lexington. Close to W&L and VMI

Simple & spacious 1-bedroom basement living in Lexington. Close to W&L and VMI
Lexington
10.0 out of 10, Exceptional, (4)
"Great location, cozy, quiet. Great accommodations "
United States
Kristen H.
The price is HK$700
HK$1,101 total
includes taxes & fees
2 Jan - 3 Jan 2026
Simple & spacious 1-bedroom basement living in Lexington. Close to W&L and VMI
Exterior
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (90)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is HK$1,011
HK$1,528 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Fridge, microwave, oven, stovetop
Rustic Romantic Bayberry Cottage at Autumn Ridge

Rustic Romantic Bayberry Cottage at Autumn Ridge

Rustic Romantic Bayberry Cottage at Autumn Ridge
Lexington
9.8 out of 10, Exceptional, (33)
"Had a great stay!"
United States
Erin C.
The price is HK$1,315
HK$2,485 total
includes taxes & fees
5 Jan - 6 Jan 2026
Rustic Romantic Bayberry Cottage at Autumn Ridge
Interior
Deerfield Honeymoon Cottage at Autumn Ridge

Deerfield Honeymoon Cottage at Autumn Ridge

Deerfield Honeymoon Cottage at Autumn Ridge
Lexington
9.8 out of 10, Exceptional, (40)
"this was such a terrific stay! very well ran and amazing hosts! "
United States
Darcy T.
The price is HK$1,609
HK$2,868 total
includes taxes & fees
5 Jan - 6 Jan 2026
Deerfield Honeymoon Cottage at Autumn Ridge
Smart TV, DVD player
Cozy Country small two bedroom home.

Cozy Country small two bedroom home.

Cozy Country small two bedroom home.
Roseland
9.8 out of 10, Exceptional, (17)
"Lovely cozy place in the mountains, we had a total blast!"
United States
Prabir
The price is HK$1,049
HK$1,912 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Country small two bedroom home.
Exterior
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Montebello
10.0 out of 10, Exceptional, (47)
"Nice quite secluded get away with great hosts that check in and make sure everything is going well. Will be staying again and definitely recommend."
United States
Ryan C.
The price is HK$1,127
HK$1,772 total
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Exterior
New Blue RIdge Mountains Montebello, Virginia with stary stary skies

New Blue RIdge Mountains Montebello, Virginia with stary stary skies

New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Montebello
10.0 out of 10, Exceptional, (19)
"Great place to get away for a few days. Short car ride to several hiking trails. "
United States
Jimmy R.
The price is HK$1,127
HK$1,772 total
includes taxes & fees
4 Jan - 5 Jan 2026
New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Exterior
Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
The price is HK$739
HK$2,170 total
includes taxes & fees
20 Jan - 21 Jan 2026
Laurelwood Hollow: Walk to Ski & Swim
Fridge, microwave, oven, stovetop
NEW! The Nest near Goshen Pass

NEW! The Nest near Goshen Pass

NEW! The Nest near Goshen Pass
2.0 star property
Rockbridge Baths
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay! There were many nice touches that made this property stand out - well-stocked kitchen, walk in shower with Native products, built in fireplace, a welcome basket. We cooked dinner one night and had everything we needed. Check in process/communication were smooth. Lee and Ian could not have been nicer. Would highly recommend for a small group or couple!"
United States
Meghan O.
The price is HK$777
HK$1,613 total
includes taxes & fees
4 Jan - 5 Jan 2026
NEW! The Nest near Goshen Pass
Exterior
Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (14)
"Great stay! Thank you!"
United States
Lauren
The price is HK$957
HK$2,200 total
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Bungalow 30 minutes from Wintergreen
Property grounds
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Buena Vista
9.0 out of 10, Wonderful, (33)
"I didn’t realize that this was an entire house with full kitchen, and two bedrooms. A wonderful place near Buena Vista and Lexington."
United States
Matthew
The price is HK$1,112
HK$2,206 total
includes taxes & fees
1 Jan - 2 Jan 2026
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Exterior
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Montebello
9.8 out of 10, Exceptional, (16)
"Absolutely loved our stay. Very relaxing time. Loved having all of the conveniences of home but being away from it all.Loved that it was dog friendly. "
United States
Leslie H.
The price is HK$1,127
HK$1,790 total
includes taxes & fees
5 Jan - 6 Jan 2026
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Interior
Water Trough Hill - Views of Lexington

Water Trough Hill - Views of Lexington

Water Trough Hill - Views of Lexington
Buena Vista
10.0 out of 10, Exceptional, (54)
"Beautiful location! We loved watching the sunset views of the hills. The home is extremely clean, always a bonus!"
United States
Julie P.
The price is HK$1,224
HK$2,003 total
includes taxes & fees
4 Jan - 5 Jan 2026
Water Trough Hill - Views of Lexington
Terrace/patio
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Nellysford
10.0 out of 10, Exceptional, (23)
"The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. "
United States
Jody W.
The price is HK$1,500
HK$3,614 total
includes taxes & fees
21 Jan - 22 Jan 2026
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
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

Howard Johnson by Wyndham Lexington

Howard Johnson by Wyndham Lexington

10/10 Excellent
"Really a fantastic hotel, totally renovated and very clean. Im very particular with where i stay and this was a 10 out of 10. Front desk was very welcoming."
Mitch 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lexington

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:

  • View our selection of featured holiday rentals in Fairfield
  • Use the map to find apartments and other holiday homes in the Fairfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Fairfield while they last

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

Frequently asked questions

Are there holiday rentals in Fairfield?

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

What are some of the best holiday rentals that Fairfield has to offer?

Upscale and Family-Friendly in Wintergreen: This holiday home rental outside of Fairfield is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Fairfield?

With 5 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Virginia Horse Center and Southern Virginia University.

What are holiday rentals like in Fairfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Fairfield. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family getaway.