Book Holiday Homes in Fairfield

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Fairfield

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Roseland
When you stay at this vacation home in Nellysford, you'll be on a lake, just steps from Wintergreen Resort and George Washington National Forest.
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

Wintergreen Resort
When you stay at this vacation home in Nellysford, you'll be in the mountains, within a 15-minute walk of Wintergreen Resort and George Washington National ...
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Insane Mountain Views - New Listing

Insane Mountain Views - New Listing

Wintergreen Resort
With a stay at this vacation home in Roseland, you'll be steps from Wintergreen Resort and George Washington National Forest.
Insane Mountain Views - New Listing
Save an average of 15% on thousands of hotels when you're signed in
Alone Mill Schoolhouse - A paradise for outdoor lovers

Alone Mill Schoolhouse - A paradise for outdoor lovers

Lexington
With a stay at this vacation home in Lexington, you'll be on the waterfront, within a 15-minute drive of Virginia Military Institute and Lexington Valley ...
Alone Mill Schoolhouse - A paradise for outdoor lovers
HOT TUB w CA King beds Acres of  & secluded. Pymt plan, dogs welcome

HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

Lexington
Located in Lexington, this vacation home is in the mountains, a 1-minute drive from Jefferson National Forest and 6 minutes from George Washington National ...
HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome
Custom Builder just completely  remodeled this Mountain Chalet! ...with Hot Tub!

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Wintergreen Resort
With a stay at this vacation home in Nellysford (Treeloft), you'll be steps from Wintergreen Resort and George Washington National Forest.
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Modern Luxury Mountain Home within Wintergreen Retreat Collection

Modern Luxury Mountain Home within Wintergreen Retreat Collection

Wintergreen Resort
With a stay at this vacation home in Nellysford (Chestnut Springs), you'll be steps from Wintergreen Resort and George Washington National Forest.
Modern Luxury Mountain Home within Wintergreen Retreat Collection
Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen Resort
The price is AU$778 per night from 14 Mar to 15 Mar
AU$778
includes taxes & fees
14 Mar - 15 Mar
When you stay at this vacation home in Nellysford, you'll be in the mountains, just steps from Wintergreen Resort and George Washington National Forest.
Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

Wintergreen Resort
With a stay at this vacation home in Nellysford (Pedlars Edge), you'll be steps from Wintergreen Resort and George Washington National Forest.
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Don't see what you're looking for?
See all available properties in Fairfield
View all properties
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.

Fairfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Fairfield vacation homes are the perfect way for you to wing it.

Holiday houses in Fairfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Fairfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Fairfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Fairfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Fairfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Fairfield Holiday Homes essential information

Accommodation
267 Holiday Homes
Lowest Price
AU$115
Highest Price
AU$778
Popular accommodation
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House., Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop, Insane Mountain Views - New Listing, Alone Mill Schoolhouse - A paradise for outdoor lovers, HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome, Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!, Modern Luxury Mountain Home within Wintergreen Retreat Collection , Spacious + Serene Mtn Top Escape, 4 En Suites, Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

Top trending hotels in Fairfield

Luxury cabin in the woods, 2 bedrooms plus loft

Luxury cabin in the woods, 2 bedrooms plus loft

Fairfield
Located in Fairfield, this cabin is in a rural location, within a 15-minute drive of Virginia Horse Center and Washington and Lee University.
Luxury cabin in the woods, 2 bedrooms plus loft
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

Fairfield
Located in Fairfield, this vacation home is in the mountains, within a 10-minute drive of Brownsburg Historic District and Rockbridge Vineyard.
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Best Western Plus Inn at Hunt Ridge

Best Western Plus Inn at Hunt Ridge

2.5 out of 5
25 Willow Springs Road, Lexington, VA
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 31 Mar to 1 Apr
AU$163
includes taxes & fees
31 Mar - 1 Apr
When you stay at Best Western Plus Inn at Hunt Ridge in Lexington, you'll be in the historical district, within a 5-minute drive of Virginia Horse Center and ...
Best Western Plus Inn at Hunt Ridge
Save an average of 15% on thousands of hotels when you're signed in
Howard Johnson by Wyndham Lexington

Howard Johnson by Wyndham Lexington

2 out of 5
2836 North Lee Highway, Lexington, VA
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 16 Mar to 17 Mar
AU$115
includes taxes & fees
16 Mar - 17 Mar
With a stay at Howard Johnson by Wyndham Lexington in Lexington, you'll be within a 10-minute drive of Virginia Military Institute and Virginia Horse ...
Howard Johnson by Wyndham Lexington
Don't see what you're looking for?
See all available properties in Fairfield
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.