Cheap Airbnb & Cabins in Winchester

Compare 14 available, short term airbnb and cabins, starts from $120

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Save Up To 74%

Best Cheap Cabins & Airbnb Deals near Winchester

Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin
7.6 (8 reviews)
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin
Cabin · 2 Guests · 1 Bedroom
$128 /night*
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Have it All, Pool with Hot Tub and Secluded Lake!
Have it All, Pool with Hot Tub and Secluded Lake!
Have it All, Pool with Hot Tub and Secluded Lake!
Have it All, Pool with Hot Tub and Secluded Lake!
Have it All, Pool with Hot Tub and Secluded Lake!
Cabin · 2 Guests · 1 Bedroom
$645 /night*
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Spacious Virginia Vacation Rental w/ Yard & Sauna
Spacious Virginia Vacation Rental w/ Yard & Sauna
Spacious Virginia Vacation Rental w/ Yard & Sauna
Spacious Virginia Vacation Rental w/ Yard & Sauna
Spacious Virginia Vacation Rental w/ Yard & Sauna
Cottage · 2 Guests · 1 Bedroom
$373 /night
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Insta Worthy Mountain Views
Insta Worthy Mountain Views
Insta Worthy Mountain Views
Insta Worthy Mountain Views
10 (3 reviews)
Insta Worthy Mountain Views
Cabin · 2 Guests · 1 Bedroom
$486 /night*
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Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!
10 (12 reviews)
Peaceful Lakefront Cottage with Mountain Views!
Cottage · 2 Guests · 1 Bedroom
$317 /night*
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Modern Chalet w Hot Tub & Game Room- Dog friendly!
Modern Chalet w Hot Tub & Game Room- Dog friendly!
Modern Chalet w Hot Tub & Game Room- Dog friendly!
Modern Chalet w Hot Tub & Game Room- Dog friendly!
6.0 (1 review)
Modern Chalet w Hot Tub & Game Room- Dog friendly!
Chalet · 2 Guests · 1 Bedroom
$194 /night*
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Whiskey Hill Cabin a mountain getaway in Virginia wine country!
Whiskey Hill Cabin a mountain getaway in Virginia wine country!
Whiskey Hill Cabin a mountain getaway in Virginia wine country!
Whiskey Hill Cabin a mountain getaway in Virginia wine country!
9.8 (49 reviews)
Whiskey Hill Cabin a mountain getaway in Virginia wine country!
Cabin · 2 Guests · 1 Bedroom
$233 /night*
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Cozy Cabin with Sunroom & Cacapon River Access!
Cozy Cabin with Sunroom & Cacapon River Access!
Cozy Cabin with Sunroom & Cacapon River Access!
Cozy Cabin with Sunroom & Cacapon River Access!
9.8 (29 reviews)
Cozy Cabin with Sunroom & Cacapon River Access!
Cabin · 2 Guests · 1 Bedroom
$137 /night*
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Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Cottage · 2 Guests · 1 Bedroom
$495 /night
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Renovated WV Schoolhouse: History Buffs Heaven!
Renovated WV Schoolhouse: History Buffs Heaven!
Renovated WV Schoolhouse: History Buffs Heaven!
Renovated WV Schoolhouse: History Buffs Heaven!
Renovated WV Schoolhouse: History Buffs Heaven!
Cottage · 2 Guests · 1 Bedroom
$155 /night
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Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!
Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!
Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!
Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!
10 (4 reviews)
Modern Chalet Cabin w Hot Tub, Deck/Grill, & WiFi!
Chalet · 2 Guests · 1 Bedroom
$216 /night*
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Peaceful Hideaway w/ Shenandoah River Access
Peaceful Hideaway w/ Shenandoah River Access
Peaceful Hideaway w/ Shenandoah River Access
Peaceful Hideaway w/ Shenandoah River Access
Peaceful Hideaway w/ Shenandoah River Access
Cottage · 2 Guests · 1 Bedroom
$235 /night
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Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
10 (10 reviews)
Front Royal Hilltop Cabin w/ Panoramic Views!
Cabin · 2 Guests · 1 Bedroom
$372 /night*
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Cozy Creekside Cabin with a Great Room
Cozy Creekside Cabin with a Great Room
Cozy Creekside Cabin with a Great Room
Cozy Creekside Cabin with a Great Room
10 (1 review)
Cozy Creekside Cabin with a Great Room
Cabin · 2 Guests · 1 Bedroom
$175 /night*
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Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
9.4 (21 reviews)
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Cabin · 2 Guests · 1 Bedroom
$1,064 /night*
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Charming Home With Yard Near Shenandoah River!
Charming Home With Yard Near Shenandoah River!
Charming Home With Yard Near Shenandoah River!
Charming Home With Yard Near Shenandoah River!
10 (1 review)
Charming Home With Yard Near Shenandoah River!
Cottage · 2 Guests · 1 Bedroom
$135 /night
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Bedrooms 2, Bathrooms 1, Sleeps 4
Bedrooms 2, Bathrooms 1, Sleeps 4
Bedrooms 2, Bathrooms 1, Sleeps 4
Bedrooms 2, Bathrooms 1, Sleeps 4
9.6 (23 reviews)
Bedrooms 2, Bathrooms 1, Sleeps 4
Cabin · 2 Guests · 1 Bedroom
$215 /night*
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Rebels Rest - Cabin with Enchanting Sunset Views!
Rebels Rest - Cabin with Enchanting Sunset Views!
Rebels Rest - Cabin with Enchanting Sunset Views!
Rebels Rest - Cabin with Enchanting Sunset Views!
10 (15 reviews)
Rebels Rest - Cabin with Enchanting Sunset Views!
Cabin · 2 Guests · 1 Bedroom
$250 /night*
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Riverfront🏕A-Frame/HOT TUB/Fire Pit🔥FAST Wifi
Riverfront🏕A-Frame/HOT TUB/Fire Pit🔥FAST Wifi
Riverfront🏕A-Frame/HOT TUB/Fire Pit🔥FAST Wifi
Riverfront🏕A-Frame/HOT TUB/Fire Pit🔥FAST Wifi
10 (23 reviews)
Riverfront🏕A-Frame/HOT TUB/Fire Pit🔥FAST Wifi
Cabin · 2 Guests · 1 Bedroom
$198 /night*
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Sunny Front Royal Vacation Rental w/ Hot Tub!
Sunny Front Royal Vacation Rental w/ Hot Tub!
Sunny Front Royal Vacation Rental w/ Hot Tub!
Sunny Front Royal Vacation Rental w/ Hot Tub!
Sunny Front Royal Vacation Rental w/ Hot Tub!
Cottage · 2 Guests · 1 Bedroom
$203 /night
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Vacation Destinations Near Winchester

Airbnb & Cabins with Full Kitchen in Winchester

Rustic Luxe. River Front. Luxury Cabin. Wild West Virginia
Rustic Luxe. River Front. Luxury Cabin. Wild West Virginia
Rustic Luxe. River Front. Luxury Cabin. Wild West Virginia
Rustic Luxe. River Front. Luxury Cabin. Wild West Virginia
Full Kitchen
10 (61 reviews)
Rustic Luxe. River Front. Luxury Cabin. Wild West Virginia
Cabin · 2 Guests · 1 Bedroom
$645 /night*
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Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!
Full Kitchen
10 (12 reviews)
Peaceful Lakefront Cottage with Mountain Views!
Cottage · 2 Guests · 1 Bedroom
$317 /night*
View deal
Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Front Royal Hilltop Cabin w/ Panoramic Views!
Full Kitchen
Front Royal Hilltop Cabin w/ Panoramic Views!
Cottage · 2 Guests · 1 Bedroom
$495 /night
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Which amenity is a must-have for cabins in Winchester?
Winchester Cabin Amenities
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Full kitchen, jacuzzi or pet friendly cabins? Or should I choose all of them? Below we write up some amenity summary for you to know more about the Winchester area. In Winchester, 2 rentals offer Full Kitchen, 1 rentals offer Air Conditioning, 1 rentals offer Heater. So, if you need Full Kitchen during your cabin stays, use the Full Kitchen filter to compare these cabins. Two amenities that are not typical are No Smoking, Internet or Wifi.

If Staying for a Week, When to Book a Cabin in Winchester?

Best Time to Book Cheapest Cabins (Stay for a Week) in Winchester

Low Season
July
Most affordable month to stay
$90
Average rate of the cheapest stay option in low season month
High Season
May
Peak month to stay
$126
Average rate of the cheapest stay option in high season month
$126
May
$106
Jun
$90
Jul
$123
Aug
$90
Sep
$90
Oct
$90
Nov
$90
Dec
$90
Jan
$90
Feb
$90
Mar
$90
Apr
$119
Sun
$125
Mon
$90
Tue
$90
Wed
$90
Thu
$90
Fri
$118
Sat
Cheapest day of week
Tuesday
Cabin price normally the lowest on this day
$90
is the cheapest nightly rate for cabin on this day
Highest day of week
Monday
Most expansive day to book a cabin
$125
is the highest nightly rate for cabin on this day
How is the cabin rental prices in Winchester?
Cabin Rentals Price Information in Winchester
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The graph shows the percentages of cabins in each price bucket. Winchester has the largest percentage (28.57%) of cabin rentals in $50 - $100 price range.
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$100 to $150
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$500 +
$500 +
Is it convenient for me to bring my pets/dogs to Winchester area?
Pet Friendly Airbnb & Cabins Percentage in Winchester
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14.29% of cabins in Winchester are pet/dog friendly. We love pets/dogs. Before booking your next cabin, make sure to filter pet friendly listings and check the number of pets allowed in the listing.
I will spend a weekend in Winchester, where should I visit?
Attractions & Things To Do in Winchester
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The POIs worth to visit near your cabin rentals in Winchester:

Trail recommendations near cabins in Winchester?
Must Visit Trails In Winchester Near Cabins
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Top trails recommended by cabin hosts in Winchester

  • Buzzard Hill Via Appalachian Trail
  • Virginia State Arboretum - Blandy Experimental Farm
  • Third Battle of Winchester Trail
  • Winchester - Warrenton Scenic Drive
  • Sky Meadows Gap Run Via North and South Ridge Loop
  • North Ridge Trail
  • Ambassador Whitehouse Trail
  • South Ridge Trail Loop
  • Piedmont Overlook Trail
  • Shockeys Knob Loop
Most recommended nearby campgrounds in Winchester?
Most Visited Campgrounds In Winchester
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Best campgrounds near cabin stays in Winchester

  • Harpers Ferry / Civil War Battlefields KOA
  • Stickpile Hill HBO Campsite
  • Purslane Run HBO Campsite
  • Candy Hill Campground
  • Huckleberry Hill HBO Campsite
  • North Fork Resort
  • Front Royal RV Campground
  • Killiansburg Cave HBO Campsite
  • Big Woods HBO Campsite
  • Opequon Junction HBO Campsite

Other Vacation Rentals Ideas

Airbnb & Cabins with Fireplace in Winchester

Bedrooms 4, Bathrooms 2, Sleeps 10
Bedrooms 4, Bathrooms 2, Sleeps 10
Bedrooms 4, Bathrooms 2, Sleeps 10
Bedrooms 4, Bathrooms 2, Sleeps 10
Fireplace
9.0 (23 reviews)
Bedrooms 4, Bathrooms 2, Sleeps 10
Cabin · 2 Guests · 1 Bedroom
$320 /night*
View deal
3 King Master Suites ~ Mountain/River VIEWS ~ Skyline Drive ~ Hiking ~ Wineries
3 King Master Suites ~ Mountain/River VIEWS ~ Skyline Drive ~ Hiking ~ Wineries
3 King Master Suites ~ Mountain/River VIEWS ~ Skyline Drive ~ Hiking ~ Wineries
3 King Master Suites ~ Mountain/River VIEWS ~ Skyline Drive ~ Hiking ~ Wineries
Fireplace
10 (163 reviews)
3 King Master Suites ~ Mountain/River VIEWS ~ Skyline Drive ~ Hiking ~ Wineries
Cabin · 2 Guests · 1 Bedroom
$275 /night*
View deal
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Fireplace
9.4 (21 reviews)
Spacious 6000SF Amazing Log Home 18acres-Hot tub-Wine Country-Hot Tub
Cabin · 2 Guests · 1 Bedroom
$1,064 /night*
View deal
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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