Title: Winchester Vacation Rentals from $218: Search Short-Term Rentals | Expedia.com

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![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester vacation rentals

![Property grounds](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/92815ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/f9fe7afa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/d94ec148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/16f6f354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Mountain Cabin, secluded, perfect for couples, near main road

[](https://www.expedia.com/Front-Royal-Hotels-Blue-Mountain-Cabin.h74077247.Hotel-Information)

Front Royal

10/10

Exceptional

(30 reviews)

"Very cozy cabin for two, great for a secluded getaway within range of great places to visit. Had everything we needed."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tom C.

$213 nightly

$235 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Blue-Mountain-Cabin.h74077247.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/7f22680b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/dbdd487f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/212d2c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/0c0a82ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

[](https://www.expedia.com/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information)

Front Royal

10/10

Exceptional

(5 reviews)

"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jay L.

$353 nightly

$390 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/13365e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/c5c32d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/1520d4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/cad5963c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain View Bungalow in Front Royal

[](https://www.expedia.com/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information)

Front Royal

10/10

Exceptional

(15 reviews)

"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brian B.

$196 nightly

$218 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/5441842b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/3bc90753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/ed3e6638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/1df4120a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly renovated Farm cottage with Mountain views 

[](https://www.expedia.com/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.Hotel-Information)

Strasburg

10/10

Exceptional

(38 reviews)

"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shannon H.

$293 nightly

$323 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/e4739be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/33aedc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/0b0b85aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/ccd121a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury tiny home farm stay on historic property with hot tub in Stephens City

[](https://www.expedia.com/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information)

Stephens City

10/10

Exceptional

(2 reviews)

"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris F.

$151 nightly

$164 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106330000/106326000/106325979/a3bac066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/107000000/106330000/106326000/106325979/b5734027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106330000/106326000/106325979/54813276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106330000/106326000/106325979/a9faaa4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dog-Friendly Cottage w Playground, Grill & Games

[](https://www.expedia.com/Middletown-Hotels-Dog-Friendly-Cottage-W-Playground.h106325979.Hotel-Information)

Middletown

9.6/10

Exceptional

(16 reviews)

"Clean cute house, exactly as described. Close to Shenandoah national park and skyline drive. Hosts very communicative "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Corrin D.

$271 nightly

$289 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Middletown-Hotels-Dog-Friendly-Cottage-W-Playground.h106325979.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/9a866bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4a296327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4383aa6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/ea22e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

[](https://www.expedia.com/Front-Royal-Hotels-Country-Cottage-Beside-Stocked-Pond-On-40-Acres-And-Blue-Ridge-Mountain-View.h51509047.Hotel-Information)

Front Royal

9.6/10

Exceptional

(17 reviews)

"Nice place, comfortable bed. Close to hiking in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jake M.

$201 nightly

$221 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Country-Cottage-Beside-Stocked-Pond-On-40-Acres-And-Blue-Ridge-Mountain-View.h51509047.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/94ade5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/233346bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, paper towels](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/37df05c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/4d2e26fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

[](https://www.expedia.com/Linden-Hotels-Cute-Cabin-Retreat-Near-Shenandoah-National-Park-And-Pet-Friendly.h96487982.Hotel-Information)

Linden

9.4/10

Exceptional

(13 reviews)

"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bret L.

$307 nightly

$339 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Linden-Hotels-Cute-Cabin-Retreat-Near-Shenandoah-National-Park-And-Pet-Friendly.h96487982.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/9afb48f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/649fbfb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/e90c6032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/a5a54162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lunar Loft, with mountain views

[](https://www.expedia.com/Bluemont-Hotels-Private-Apartment-On-A-Beautiful-Private-Farm.h83591191.Hotel-Information)

Bluemont

8.8/10

Excellent

(6 reviews)

"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Haley M.

$237 nightly

$270 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Bluemont-Hotels-Private-Apartment-On-A-Beautiful-Private-Farm.h83591191.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/a6d1f136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/1ca53946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/4181fefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/97da5da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cameron Charmer pristine downtown apt with double master suites 

[](https://www.expedia.com/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.Hotel-Information)

Winchester

9.4/10

Exceptional

(6 reviews)

"Nice house in a good central location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mitchell V.

$308 nightly

$349 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/93000000/92030000/92029800/92029786/95696cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92030000/92029800/92029786/c44da385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92030000/92029800/92029786/fa0263e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92030000/92029800/92029786/85a3d76e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hidden Gem on Hidden Valley Lane

[](https://www.expedia.com/Linden-Hotels-Hidden-Gem-On-Hidden-Valley-Lane.h92029786.Hotel-Information)

Linden

9.6/10

Exceptional

(27 reviews)

"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa W.

$423 nightly

$454 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Linden-Hotels-Hidden-Gem-On-Hidden-Valley-Lane.h92029786.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/c7a94a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/1b928033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/b00d8fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/902ff11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nostalgia Lane in the heart of the city

[](https://www.expedia.com/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information)

Old Town Winchester

9.0/10

Wonderful

(15 reviews)

"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tracy F.

$293 nightly

$332 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/71000000/70970000/70964200/70964165/c13c3812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70970000/70964200/70964165/1a42045e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70970000/70964200/70964165/c64c52e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70970000/70964200/70964165/6b42b33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Pond Cabin: Hot Tub & Stocked Pond

[](https://www.expedia.com/Linden-Hotels-The-Pond-Cabin-Hot-Tub-Stocked-Pond.h70964165.Hotel-Information)

Linden

10/10

Exceptional

(34 reviews)

"It was the perfect home away from home in a place that allowed our little family to take a breath of nature and just be. Close enough to many fun adventures. The amenities provided on the property also kept us very busy!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brena H.

$467 nightly

$515 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Linden-Hotels-The-Pond-Cabin-Hot-Tub-Stocked-Pond.h70964165.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/26f8fc5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/27dccfa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/ecb68d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/20bcdff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Skyland Hideaway | Mountain Cabin w/ Hot Tub

[](https://www.expedia.com/Linden-Hotels-Skyland-Hideaway-Mountain-Cabin-W-Hot-Tub.h87568647.Hotel-Information)

Linden

10/10

Exceptional

(15 reviews)

"As described. Enjoyed the cleanliness, hot tub, coziness of the cabin. Host was available if needed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roger M.

$370 nightly

$408 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Linden-Hotels-Skyland-Hideaway-Mountain-Cabin-W-Hot-Tub.h87568647.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/491c0c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/65278110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/164fdddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/d041791b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Indigo Blue modern open vibe on tree lined street

[](https://www.expedia.com/Winchester-Hotels-Indigo-Blue-Modern-Open-Vibe-On-Tree-Lined-Street.h75832658.Hotel-Information)

Winchester Historic District

10/10

Exceptional

(13 reviews)

"Perfect for our needs for our daughter’s graduation!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris and Michelle P.

$355 nightly

$402 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Indigo-Blue-Modern-Open-Vibe-On-Tree-Lined-Street.h75832658.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/85e7a007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/8df6db80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/52f36c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/01e432da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain cottage w/hot tub & fire pit

[](https://www.expedia.com/Front-Royal-Hotels-Hot-Tub.h60275491.Hotel-Information)

Front Royal

9.0/10

Wonderful

(31 reviews)

"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elissa S.

$282 nightly

$302 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Hot-Tub.h60275491.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/a1cdbec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/7f25e5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/4d5adcbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/fac5b632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Juniper Cabin • Cozy Hideaway w/ Hot Tub

[](https://www.expedia.com/Linden-Hotels-The-Juniper-Cabin-Cozy-Hideaway-W-Hot-Tub.h91195541.Hotel-Information)

Linden

10/10

Exceptional

(22 reviews)

"We had a fantastic time staying at this property for the weekend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Colin N.

$340 nightly

$374 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Linden-Hotels-The-Juniper-Cabin-Cozy-Hideaway-W-Hot-Tub.h91195541.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f7d693d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c2c2b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/3d395fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f8332737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Vue - Mountain Top hot tub overlooking the Shenandoah River

[](https://www.expedia.com/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information)

Front Royal

10/10

Exceptional

(16 reviews)

"We had a phenomenal stay! The view was absolutely breathtaking, and the house was well-kept and comfortable. We’re already talking about our next trip!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dan P.

$364 nightly

$401 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/10cae090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/fb3e185f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/8ba4a64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/6e67f714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain cabin near national park & wineries

[](https://www.expedia.com/Linden-Hotels-Mountain-Cabin-Near-National-Park-Wineries.h87694517.Hotel-Information)

Linden

10/10

Exceptional

(28 reviews)

"The house and location were perfect for a little getaway with friends. It was very clean, and the location was great! We were very pleased with the entire experience."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer d.

$383 nightly

$422 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Linden-Hotels-Mountain-Cabin-Near-National-Park-Wineries.h87694517.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/4d7efd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/b99b52d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/ddb97a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/3db057ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Apple Mountain House

[](https://www.expedia.com/Front-Royal-Hotels-The-Apple-Mountain-House.h113933293.Hotel-Information)

Front Royal

9.6/10

Exceptional

(10 reviews)

"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Katia R.

$356 nightly

$393 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-The-Apple-Mountain-House.h113933293.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-16&endDate=2026-03-17&regionId=6056879&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CABIN)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APARTMENT)

Private vacation homes

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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=COTTAGE)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CHALET)

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## Top Winchester Hotel Reviews

![Quality Inn Harpers Ferry - Charles Town](https://images.trvl-media.com/lodging/1000000/30000/25200/25179/e301290f_y.jpg)

### Quality Inn Harpers Ferry - Charles Town

10/10 Excellent

"The room was comfortable and clean, and having breakfast included was great. Also, it’s very convenient being only a few minutes away from the main historic area of Harpers Ferry. "

[](https://expedia.com/Martinsburg-Hotels-Quality-Inn.h25179.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg)

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Nice facility, nice staff, and comfortable clean room. Superior exercise room. Suggest removing broken/non-functioning bottle fed water cooler in exercise room and having signage direct guests to water fountain “just around the corner by the elevator.“ Warm breakfast adequate and served in very comfortable, bright area. The only bill downside was fellow guests who were traveling with dogs. Despite the hotel, providing waste bags, prominently and posting signs asking guests to “pick up after your dog, please,” there was a grotesque amount of dog droppings all around the hotel exterior."

[](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)

![Candlewood Suites Winchester by IHG](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398_y.jpg)

### Candlewood Suites Winchester by IHG

10/10 Excellent

"Love the rooms and when the stove broke, they came and fixed it immediately"

[](https://expedia.com/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information)

![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg)

### Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"Room was clean and it was easy to check in. Breakfast in the morning was good and easy to check out also."

[](https://expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information)

![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/c1c4db32_y.jpg)

### Hampton Inn Martinsburg

10/10 Excellent

"Very friendly staff, clean, breakfast is bangin. I stayed here for more than 2 weeks and had no problems whatsoever"

[](https://expedia.com/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information)

![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg)

### Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"Staff was great! Will go back"

[](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)

![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/b8108f6b_y.jpg)

### Hilton Garden Inn Dulles North

10/10 Excellent

"Staff was very friendly, always enjoy this property."

[](https://expedia.com/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information)

![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a_y.jpg)

### SpringHill Suites by Marriott Winchester

10/10 Excellent

"The pool was warm, and everything was very clean. The staff were also great! "

[](https://expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information)

![Fairfield Inn & Suites by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/0de00556_y.jpg)

### Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"Room was clean. Check-in was quick and courteous. Breakfast was what we needed."

[](https://expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information)

## Find out more about Winchester

**Everything you need to know about Winchester vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winchester vacation rentals: An excellent choice for every season**

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $218 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Winchester rentals**

At Expedia, we put the best Winchester vacation 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 Winchester 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 Winchester vacation.

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

## Explore a world of travel with Expedia

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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d6056879-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchester ](https://expedia.com/Winchester-Cabins.d6056879-aaCabins.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d6056879-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.com/Winchester-Cottages.d6056879-aaCottages.Travel-Guide-Accommodation)
- [Chalets in Winchester ](https://expedia.com/Winchester-Chalets.d6056879-aaChalets.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.com/Winchester-Agritourism.d6056879-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.com/Winchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.com/Winchester-Motels.d6056879-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Winchester ](https://expedia.com/Winchester-Guest-Houses.d6056879-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Winchester ](https://expedia.com/Winchester-Villas.d6056879-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Winchester ](https://expedia.com/Winchester-Lodges.d6056879-aaLodges.Travel-Guide-Accommodation)
- [Resorts in Winchester ](https://expedia.com/Winchester-Resorts.d6056879-aaResorts.Travel-Guide-Accommodation)
- [RV Parks in Winchester ](https://expedia.com/Winchester-RV-Parks.d6056879-aaRVParks.Travel-Guide-Accommodation)
- [Inns in Winchester ](https://expedia.com/Winchester-Inns.d6056879-aaInns.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.com/Winchester-Condos.d6056879-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Winchester?

### What are some of the best vacation home rentals in Winchester?

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- [Hotels in Fairfax](https://expedia.com/Fairfax-Hotels.d8062.Travel-Guide-Hotels)
- [Hotels in Blacksburg](https://expedia.com/Blacksburg-Hotels.d6056941.Travel-Guide-Hotels)
- [Hotels in Harrisonburg](https://expedia.com/Harrisonburg-Hotels.d6056902.Travel-Guide-Hotels)
- [Cheap Hotels in Virginia Beach](https://expedia.com/Virginia-Beach-Hotels-Cheap-Hotels.0-0-d10271-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Alexandria](https://expedia.com/Alexandria-Hotels.d5980.Travel-Guide-Hotels)
- [Hotels in Charlottesville](https://expedia.com/Charlottesville-Hotels.d6057012.Travel-Guide-Hotels)
- [Hotels in Norfolk](https://expedia.com/Norfolk-Hotels.d2689.Travel-Guide-Hotels)
- [Hotels in Fredericksburg](https://expedia.com/Fredericksburg-Hotels.d8145.Travel-Guide-Hotels)
- [Hotels in Chincoteague](https://expedia.com/Chincoteague-Hotels.d55637.Travel-Guide-Hotels)
- [Hotels in Danville](https://expedia.com/Danville-Hotels.d6056951.Travel-Guide-Hotels)
- [Hotels in Lynchburg](https://expedia.com/Lynchburg-Hotels.d2187.Travel-Guide-Hotels)
- [Hotels in Newport News](https://expedia.com/Newport-News-Hotels.d6056964.Travel-Guide-Hotels)
- [Hotels in Virginia Beach](https://expedia.com/Virginia-Beach-Hotels.d10271.Travel-Guide-Hotels)
- [Hotels in Roanoke](https://expedia.com/Roanoke-Hotels.d3020.Travel-Guide-Hotels)
- [Oceanfront Hotels in Virginia Beach](https://expedia.com/Virginia-Beach-Hotels-Oceanfront-Hotels.0-0-d10271-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Hampton](https://expedia.com/Hampton-Hotels.d6067.Travel-Guide-Hotels)
- [Hotels in Williamsburg](https://expedia.com/Williamsburg-Hotels.d6296.Travel-Guide-Hotels)
- [Pet-friendly Hotels in Virginia Beach](https://expedia.com/Virginia-Beach-Hotels-Pet-Friendly-Hotel.0-0-d10271-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Chesapeake](https://expedia.com/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)

Flights

- [Cheap Flights to Syria](https://expedia.com/Cheap-Flights-To-Syria.d184113.Travel-Guide-Flights)
- [Cheap Flights to Roanoke](https://expedia.com/Cheap-Flights-To-Roanoke.d3020.Travel-Guide-Flights)
- [Cheap Flights to Virginia Beach](https://expedia.com/Cheap-Flights-To-Virginia-Beach.d10271.Travel-Guide-Flights)
- [Cheap Flights to Charlottesville](https://expedia.com/Cheap-Flights-To-Charlottesville.d6057012.Travel-Guide-Flights)

Cars

- [Car rentals in Newport News](https://expedia.com/Car-Rentals-In-Newport-News.d6056964.Car-Rental-Guide)
- [Car rentals in Virginia Beach](https://expedia.com/Car-Rentals-In-Virginia-Beach.d10271.Car-Rental-Guide)
- [Car rentals in Alexandria](https://expedia.com/Car-Rentals-In-Alexandria.d5980.Car-Rental-Guide)

Activities

- [Things to do in Norfolk](https://expedia.com/Things-To-Do-In-Norfolk.d2689.Travel-Guide-Activities)

Packages

- [Virginia Beach Vacation](https://expedia.com/Virginia-Beach.d10271.Destination-Travel-Guides)

Vacation Rentals

- [Virginia Beach Vacation Rentals](https://expedia.com/Virginia-Beach-Vacation-Rentals.d10271.Travel-Guide-VacationRentals)

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