Hot Winchester Cottage Rates

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Featured Cottages in Winchester

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg
The price is AU$637 per night from 20 Mar to 21 Mar
AU$637
includes taxes & fees
20 Mar - 21 Mar
With a stay at this cottage in Middleburg, you'll be within a 10-minute drive of National Sporting Library & Museum and Tudor Day Spa.
18th Century Stone Cottage minutes from historic Middleburg
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Luray
The price is AU$523 per night from 16 Mar to 17 Mar
AU$523
includes taxes & fees
16 Mar - 17 Mar
With a stay at this cottage, you'll be centrally located in Luray, within a 10-minute drive of Luray Caverns and Shenandoah National Park.
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Carrot Top Cottage surrounded by National Park

Carrot Top Cottage surrounded by National Park

Harpers Ferry
Located in Harpers Ferry, this cottage is within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races.
Carrot Top Cottage surrounded by National Park
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Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

Purcellville
This cottage is 17.6 mi (28.4 km) from Hollywood Casino at Charles Town Races and 0.3 mi (0.5 km) from Franklin Park.
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage

Harpers Ferry
The price is AU$286 per night from 24 Mar to 25 Mar
AU$286
includes taxes & fees
24 Mar - 25 Mar
With a stay at this cottage in Harpers Ferry, you'll be within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town ...
The Carriage House at Carrot Top Cottage
Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg

Leesburg
The price is AU$762 per night from 26 Mar to 27 Mar
AU$762
includes taxes & fees
26 Mar - 27 Mar
A stay at this cottage places you in the heart of Leesburg, steps from Catoctin Valley and 2 minutes by foot from Dodona Manor.
Royal Heritage Home @ Historic Leesburg
Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets

Fort Valley
Located in Fort Valley, this cottage is a 1-minute drive from George Washington National Forest and 10 minutes from Massanutten Storybook Trail.
Cozy Retreat - Hot tub + Mountain Views + Pets
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2 out of 5
Harpers Ferry
With a stay at this cottage in Harpers Ferry, you'll be a 2-minute drive from Harpers Ferry National Historical Park and 10 minutes from Hollywood Casino at ...
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

Luray
Located in Luray, this cottage is in a rural location, within a 10-minute drive of Yogi Bear's Jellystone Park and Shenandoah National Park.
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
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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.

Winchester Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Winchester will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Winchester definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Winchester, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Winchester Cottages essential information

Accommodation
148 Cottages
Lowest Price
AU$119
Highest Price
AU$762
Popular accommodation
18th Century Stone Cottage minutes from historic Middleburg, Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*, Carrot Top Cottage surrounded by National Park, Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond, The Carriage House at Carrot Top Cottage, Royal Heritage Home @ Historic Leesburg, Cozy Retreat - Hot tub + Mountain Views + Pets, Amazing dog-friendly cottage. Walk 2 Harpers Ferry, Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

Top trending hotels in Winchester

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 6 Apr to 7 Apr
AU$162
includes taxes & fees
6 Apr - 7 Apr
With a stay at La Quinta Inn & Suites by Wyndham Winchester in Winchester, you'll be in the business district, just a 3-minute walk from Shenandoah University ...
La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 17 Mar to 18 Mar
AU$138
includes taxes & fees
17 Mar - 18 Mar
Located in Winchester, Microtel Inn & Suites by Wyndham Winchester is within a 10-minute drive of Jim Barnett Park and Winchester Medical Center.
Microtel Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St, Winchester, VA
The price is AU$225 per night from 14 Mar to 15 Mar
AU$225
includes taxes & fees
14 Mar - 15 Mar
The George Washington Hotel, A Wyndham Grand Hotel is centrally located in Winchester, a 4-minute walk from Handley Regional Library and 9 minutes by foot from ...
The George Washington Hotel, A Wyndham Grand Hotel
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Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
140 Costello Dr, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 23 Mar to 24 Mar
AU$119
includes taxes & fees
23 Mar - 24 Mar
A stay at Sleep Inn & Suites places you in the heart of Winchester, steps from Valley Health and a 2-minute drive from Shenandoah University.
Sleep Inn & Suites
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.