Title: Winchester Vacation Rentals from $219: 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 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-06-19&endDate=2026-06-21&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)

![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)

![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)

![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.

$214 nightly

$236 total

Mar 1 - Mar 2

Total with taxes and fees

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

![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)

![TV, books](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/e073d995.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)

### 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 1 - Mar 2

Total with taxes and fees

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

![TV](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/df4a0d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/de9610ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/512057d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/63a92e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Front royal majestic paradise

[](https://www.expedia.com/Front-Royal-Hotels-Front-Royal-Majestic-Paradise.h120444425.Hotel-Information)

Front Royal

$1,398 nightly

$1,542 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Front-Royal-Majestic-Paradise.h120444425.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/76000000/75860000/75857000/75856945/97da5da1.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)

### 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 1 - Mar 2

Total with taxes and fees

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

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/88d4dc47.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

(13 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.

$197 nightly

$219 total

Mar 1 - Mar 2

Total with taxes and fees

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

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

![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/234bd7f2.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)

### 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 1 - Mar 2

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)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w506h683x260y0-1afec896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/3aaa43b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w507h683x259y0-313a4f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w506h683x259y0-d4dd74ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Very charming & spacious 2 bedrm

[](https://www.expedia.com/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information)

Winchester

$171 nightly

$186 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/7c748bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/dda7ab71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/2736c2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, stovetop](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/a6f1e321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Riverfront Home Getaway with Hot Tub

[](https://www.expedia.com/Front-Royal-Hotels-Luxury-Riverfront-Home-Getaway-With-Hot-Tub.h121418475.Hotel-Information)

Warren County

$466 nightly

$484 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Luxury-Riverfront-Home-Getaway-With-Hot-Tub.h121418475.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/125000000/124800000/124797900/124797846/144bb2a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124800000/124797900/124797846/a5ef12ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124800000/124797900/124797846/0ec37f03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124800000/124797900/124797846/2477f602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bluemont home just minutes to wineries, breweries, hiking and more!

[](https://www.expedia.com/Bluemont-Hotels-Bluemont-Home-Just-Minutes-To-Wineries.h124797846.Hotel-Information)

Bluemont

$393 nightly

$438 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Bluemont-Hotels-Bluemont-Home-Just-Minutes-To-Wineries.h124797846.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)

![Property grounds](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4383aa6d.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)

![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 dining](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/3a15610b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/e9d00149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/0debe0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/f205a55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shenandoah Twilight | Cozy Cabin w/ hot tub

[](https://www.expedia.com/Front-Royal-Hotels-Shenandoah-Twilight-Cozy-Cabin-W-Hot-Tub.h104082014.Hotel-Information)

Front Royal

9.0/10

Wonderful

(2 reviews)

"Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. "

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

Wilson (Wally) W.

$401 nightly

$442 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Shenandoah-Twilight-Cozy-Cabin-W-Hot-Tub.h104082014.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)

![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)

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

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/2359633a.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 1 - Mar 2

Total with taxes and fees

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

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

![Microwave, oven, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/3e63ad06.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 2 - Mar 3

Total with taxes and fees

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89800000/89792300/89792293/b8ee4a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89800000/89792300/89792293/0344fe88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89800000/89792300/89792293/04765dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/90000000/89800000/89792300/89792293/b47a597b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spring Retreat! Hot tub, Bar, Game room, Grill & 10 mins to Skyline Drive

[](https://www.expedia.com/Front-Royal-Hotels-Spacious-Home-Near-Natl-Park.h89792293.Hotel-Information)

Front Royal

9.8/10

Exceptional

(34 reviews)

"Great place to stay. Will go back! Thanks "

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

Gareth E.

$588 nightly

$648 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Spacious-Home-Near-Natl-Park.h89792293.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)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/144b7449.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)

![Interior](https://images.trvl-media.com/lodging/76000000/75840000/75832700/75832658/164fdddc.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 2 - Mar 3

Total with taxes and fees

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

![TV, fireplace](https://images.trvl-media.com/lodging/126000000/125450000/125448300/125448222/a6f39c6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/126000000/125450000/125448300/125448222/9002826d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/126000000/125450000/125448300/125448222/d73cdc49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/126000000/125450000/125448300/125448222/84d2642b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 25 min to SNP Forest Views, Deck and Game Lounge

[](https://www.expedia.com/Front-Royal-Hotels-25-Min-To-SNP-Forest-Views.h125448222.Hotel-Information)

Shenandoah Farms

$508 nightly

$560 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-25-Min-To-SNP-Forest-Views.h125448222.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/63526894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/2f7695a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/6d4d454a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/197f6c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Riverfront! Shenandoah River! Sleeps 4! New Hot Tub 

[](https://www.expedia.com/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.Hotel-Information)

Front Royal

9.8/10

Exceptional

(14 reviews)

"Excellent place to stay. Shelly is an excellent host. Nice location "

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

Lisa H.

$387 nightly

$430 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/26a9ad25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/dffc6319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/6e3d67f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/1c0f432c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!

[](https://www.expedia.com/Front-Royal-Hotels-Cozy-Bear-Cabin-Hot-Tub.h112549200.Hotel-Information)

Front Royal

10/10

Exceptional

(4 reviews)

"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "

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

grace g.

$600 nightly

$662 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Front-Royal-Hotels-Cozy-Bear-Cabin-Hot-Tub.h112549200.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/d5eb0f37.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.

$348 nightly

$384 total

Mar 1 - Mar 2

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)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/e0ae9bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/4ef124d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/aac25142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/49b61b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Scarborough Fair walk to downtown two story apt

[](https://www.expedia.com/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information)

Old Town Winchester

9.8/10

Exceptional

(6 reviews)

"Excellent location, easy walk to most of the Old Town area. Michele is a great host, will definitely stay here again if in the area. "

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

Larry E.

$346 nightly

$392 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.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=2026-03-12&endDate=2026-03-13&regionId=6056879&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=CABIN)

Private vacation homes

[](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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VACATION_HOME)

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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=COTTAGE)

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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APARTMENT)

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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&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=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=CHALET)

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## Top Winchester Hotel Reviews

![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/1000000/70000/63100/63064/835cd022_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)

![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_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/w4000h2662x0y0-b556d792_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)

![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

"201 "

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

"Clean convient and quiet"

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

![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275_y.jpg)

### Sleep Inn & Suites Winchester near University

10/10 Excellent

"Room was clean "

[](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information)

![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg)

### The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"Fantastic "

[](https://expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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

"Very nice hotel. Everything was seamless "

[](https://expedia.com/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.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 $219 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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- [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?

### How many vacation rentals will I find in Winchester?

### What’s there to see and do in Winchester?

### What’s a vacation rental in Winchester like?

### Expedia's Latest Trends

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- [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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