Holiday Rentals in Fairfield

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Our top choices for Fairfield holiday rentals

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

Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge
Fairfield
9.8 out of 10, Exceptional, (12 reviews)
"Always have a great stay here. Views are spectacular! Lots of space for families. "
United States
Ellen H.
The price is €449
includes taxes & fees
17 May - 18 May
Fall Foliage Views + Hot Tub Escape near WLU & VMI at Sunrise Ridge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
The price is €191
includes taxes & fees
18 May - 19 May
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (32 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is €284
includes taxes & fees
18 May - 19 May
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (59 reviews)
"The place & everything was great!"
United States
Major G.
The price is €205
includes taxes & fees
28 May - 29 May
Whimsical Creekside Cabin

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, (58 reviews)
"Beautiful location, great hosts, perfect trip. If you’re looking for a quiet getaway, this is the place. "
United States
Adam L.
The price is €201
includes taxes & fees
17 May - 18 May
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

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, (103 reviews)
"This place is such a gem. Stunning property, clean, and comfortable. You can tell the hosts take a lot of pride in this place. Loved it. "
United States
Warren
The price is €173
includes taxes & fees
17 May - 18 May
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"
United States
Meredith T.
The price is €201
includes taxes & fees
17 May - 18 May
Where the Trail Ends

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (16 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is €252
includes taxes & fees
17 May - 18 May
Historic Bungalow 30 minutes from Wintergreen

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
9.8 out of 10, Exceptional, (28 reviews)
"Nice and cozy home for overnight stays "
United States
Yahima O.
The price is €167
includes taxes & fees
8 Jun - 9 Jun
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail

New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
Montebello
9.4 out of 10, Exceptional, (10 reviews)
"The property was very clean and located on scenic property. The owner provided many extra perks such as firewood, fire pit, grill, cooking materials, and several toiletries! Would definitely recommend this location to anyone!"
United States
Donna
The price is €201
includes taxes & fees
17 May - 18 May
New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (153 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is €217
includes taxes & fees
19 May - 20 May
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

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, (20 reviews)
"Beautiful cabin in a lovely setting. Already planning another visit during warmer weather so we can take advantage of all the nearby outdoor activities."
United States
Michael C.
The price is €201
includes taxes & fees
17 May - 18 May
New Blue RIdge Mountains Montebello, Virginia with stary stary skies

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is €270
includes taxes & fees
21 May - 22 May
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

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, (19 reviews)
"Heat works great. Very pet friendly. "
United States
Barbara L.
The price is €201
includes taxes & fees
17 May - 18 May
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is €230
includes taxes & fees
18 May - 19 May
Wintergreen Condo -Steps to Ski and restaurants

Kennedy Ridge Cabin--1BR, jacuzzi, kitchenette

Kennedy Ridge Cabin--1BR, jacuzzi, kitchenette
Lyndhurst
The price is €205
includes taxes & fees
20 May - 21 May
Kennedy Ridge Cabin--1BR, jacuzzi, kitchenette

Cozy Country small two bedroom home.

Cozy Country small two bedroom home.
Roseland
9.8 out of 10, Exceptional, (19 reviews)
"Lovely cozy place in the mountains, we had a total blast!"
United States
Prabir
Cozy Country small two bedroom home.

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (60 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is €102
includes taxes & fees
24 May - 25 May
The Firefly Springhouse

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (103 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
The price is €232
includes taxes & fees
25 May - 26 May
Endless Mountain Top Views from All The Way Up!

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, (38 reviews)
"Great stay. Nice property in a very quiet neighborhood. "
United States
Kurtis W.
The price is €178
includes taxes & fees
20 May - 21 May
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
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

Find out more about Fairfield

Everything you need to know about Fairfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fairfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fairfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Fairfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fairfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fairfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fairfield holiday rentals we have selected for you start as low as €167 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Fairfield rentals

At Expedia, we put the best Fairfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Fairfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fairfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fairfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia: This highly rated holiday home rental in 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 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.