Berryville vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Berryville

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best Berryville vacation rentals

Most recommended vacation rentals in Berryville

Show all
The Outpost Suite 3 - Whimsical Farmhouse Retreat - Berryville - Bedroom
The Outpost Suite 3 - Whimsical Farmhouse Retreat
Berryville, VA
Pet friendly
$254+
Check availability
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch - Berryville - Living room
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch
Berryville, VA
Free Wi-Fi
Pet friendly
$622+
Check availability
Family Retreat with Deck Near Appalachian Trail! - Berryville - Patio
Family Retreat with Deck Near Appalachian Trail!
Berryville, VA
Free Wi-Fi
Pet friendly
$712+
Check availability
The Outpost Suite 2- A Curated Farmhouse Suite - Berryville - Bedroom
The Outpost Suite 2- A Curated Farmhouse Suite
Berryville, VA
Pet friendly
$250+
Check availability
Pet-Friendly Berryville Home Walk to Main Street! - Berryville - Dining room
Pet-Friendly Berryville Home Walk to Main Street!
Berryville, VA
9.9Wonderful(10)
Free Wi-Fi
Pet friendly
$318+
Check availability
Stunning Former Winery with Pool and Mtn Views! - Berryville - Building
Stunning Former Winery with Pool and Mtn Views!
Berryville, VA
Free Wi-Fi
Pool
Pet friendly
$1,677+
Check availability
Peaceful Riverfront Retreat with Yoga and Art Studio! - Berryville - Living room
Peaceful Riverfront Retreat with Yoga and Art Studio!
Berryville, VA
Free Wi-Fi
$282+
Check availability
Mountain View Cottage @ 66-acre Horse Farm - Berryville - Patio
Mountain View Cottage @ 66-acre Horse Farm
Berryville, VA
$473+
Check availability
13 BR Boutique in Berryville - Berryville - Bedroom
13 BR Boutique in Berryville
Berryville, VA
$1,410+
Check availability
Modern House Barn @ 66 acre- Horse Farm - Berryville - Living room
Modern House Barn @ 66 acre- Horse Farm
Berryville, VA
Free Wi-Fi
$257+
Check availability
Charming 4-bedroom Estate - A Historic Gem in Clarke County, VA - Berryville - Kitchen
Charming 4-bedroom Estate - A Historic Gem in Clarke County, VA
Berryville, VA
$965+
Check availability
Suite 4: Outpost · Gorgeous Farm Carriage House Loft - Berryville - Bedroom
Suite 4: Outpost · Gorgeous Farm Carriage House Loft
Berryville, VA
$267+
Check availability
Smithfield Farm B&B - Berryville
Smithfield Farm B&B
Berryville, VA
10Wonderful(3)
Free Wi-Fi
$287+
Check availability
Riverfront Getaway w/ Breathtaking Views! - Berryville
Riverfront Getaway w/ Breathtaking Views!
Berryville, VA
$242+
Check availability
Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$0 - $420$420 - $839$839 - $1,258$1,258 - $1,677$1,677+ per night

Property Types

ApartmentCottageHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet
Useful Info

Good to know

Low season

February

High season

April

Average price (weekend night)

$278
Cheapest month to stay with an average 74% drop in price.
Most expensive month to stay with an average 74% rise in price.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Berryville vacation rental deals

  • The best vacation rental properties in Berryville are Family Retreat with Deck Near Appalachian Trail! (9.9, 30 reviews), Riverfront Getaway w/ Breathtaking Views! (9.7, 45), and The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch (8.2, 20), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Berryville, you should consider visiting during the low season. The cheapest vacation homes in Berryville can be found in February and April.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Berryville for 17 days.

FAQs when booking a vacation home in Berryville

  • What types of vacation rentals are available in Berryville?

    There are loads of different property types that you can make your vacation home in Berryville. You’ll find apartments, farm stays and houses.

  • What are some of the most-loved vacation rentals available in Berryville?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Smithfield Farm B&B.

  • Are there any pet-friendly vacation rentals in Berryville?

    There are a number of dog and pet-friendly Berryville vacation rentals, with around 32% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Berryville?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Berryville?

Our map will help you find the perfect place to stay in Berryville by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Berryville

Berryville vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Berryville. Find cheap vacation homes to rent in Berryville. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Berryville that suits you best.

Not what you’re looking for? Find thousands of other hotels, airline tickets, car rentals and package deals with KAYAK.