
Cottage vacation rentals in Winchester
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Winchester
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester cottage rentals
Cottage rentals with a hot tub

Spacious Mtn Pet Friendly Home + Hottub + Firepit*
This house was a great fit for 8 adults (four couples) staying in the area to explore Harper’s Ferry. Our main criteria was four bedrooms, a hot tub, fire pit, and not too far from the main attractions. The house checked all these boxes and was comfortable to hang out at and relax all together and cook meals, and close enough to the key things in the area we came out that way to do. Bonus points for the Mountain Lake Club being so close to the house & a very convenient spot to grab dinner Friday night when we arrived. The house was a bit light on paper products like extra toilet paper and paper towels, and there wasn’t a kitchen towel, so I would suggest packing extras for your stay here. There was also a local country store very close by to pick those things up. There were JUST enough towels for the 8 of us, so with the hot tub, might be worth packing some extras as well. Beds were comfortable & clean. Would definitely recommend this AirBnB to others, and would stay here again.

Holly Tree Retreat Located In Beautiful Luray, VA.
Wonderful place to stay. We really enjoyed how clean the place was and how accommodating Jennifer was. The place is very cozy and the attention to detail is impeccable. We loved staying here. After two really bad experiences with AirBnBs this place really changed our attitudes. Jennifer was very responsive and very helpful. Would recommend this place to anybody! Wonderful home away from home!

Shenandoah River Chalet❤️fire pit tubes/deck
We had an incredible stay at this beautiful cabin in the woods! The location was peaceful and secluded, yet still easy to get to. Dave and Melissa were super helpful and responsive and offered great local recommendations. They made sure we had everything we needed and went above and beyond to make our stay comfortable.

Cozy Cottage in the heart of Berkeley Springs WV
They are the perfect hosts. If we’re ever to start my own Airbnb I would take notes from these amazing hosts. I use Airbnb very often and have stayed at many places. This was by far my most comfortable and welcomed stay in all of my travels. Top notch job to Emily and Heather. They truly get it and it is like they designed their experience after thinking about what they would want. I can’t say enough about how welcomed they make you feel. The cottage is beautiful and even though I did not bring any of my kitties with me, but this place is the most pet friendly place I have ever heard about or witnessed!! Thank you to you both and you will see me and Heather again. I will gladly recommend your cottage to anyone that asks me where to stay in Berkeley Springs. Or anywhere peaceful and relaxing. You guys pamper your guests which is refreshing.

Vibrant Cottage | Hot Tub | Pets | Shenandoah NP
Excellent Communication - Beautiful Home - Perfect Location !! OLIVIA SAVED THE DAY !!!!!!!!!! Initially I had another air bnb location booked. When we arrived the location was nothing like the pictures. Where we expected lush green views what we saw was overall very desolate and "spooky". I canceled and immediately started searching for another place. This trip was a birthday celebration for my wife and I really wanted to get everything right ! Olivia responded fast and allowed us to check in same day with only an hours notice. We were pleasantly surprised by how aesthetically intriguing the house was , the color palette's she chose throughout the house are MARVELOUS ! The jacuzzi worked 100% as well as all of the other appliances. You can really see that care and attention to detail where put into this home , which ultimately made us feel at home ! I'd 100% book again with Olivia . We have already started planning our next trip to our getaway at the Vibrant Cottage !

The 3R's River, Relaxation, Retreat + hot tub
What an awesome host, was there to greet and explain the property in great detail. Will definitely be back!

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!
James is a gracious host very attentive and gives plenty of detailed information before the visit to be able to navigate and know what's coming. I appreciate it as a super host myself. I know what it takes to make sure people are informed about everything and he does a lovely job.

Uber SXY Private Country Escape! Hot Tub & Views~
If i could put a price on piece of mind and tranquility, I'd say we underpaid. Best reset in a long time (and we reset often). This was my husband and my second stay at one of Ms. Gillian's properties and we haven't been the slightest of disappointed .. Each stay she went above and beyond and was even able to accommodate us at the very last minute with every bell and whistle on point. The pictures posted are an understatement to the relaxation it provided.
Pet-friendly cottage rentals

Rappahannock River Cottage Near I-95 Sleeps 6!
nice comfortable stay. felt like I was out in the country staying at a friend's house. thanks Patty!

Wine Country Cottage
We had a great time at Lisa’s place! Everything was exactly like the pictures, and her host guidebook was such a nice touch to have! Easy to get an uber and surrounded by local breweries and wineries, and hiking trails. The place was very clean and such a cute location. We would stay here again.

Cozytown Cottage/Whitetail Ski Resort/Hagerstown
I love the peace and tranquillity at Jens place! I brought my teenage grandson along for a trip to the country and some time for us to connect away from it all. We spent time doing one of the puzzles at the house and relaxing. It was amazing to see him let down the “teenage edge” in the cozy atmosphere her cottage provides. While out and about one evening we stumbled upon what is an annual Christmas Tree lighting in the town square of Greencastle. What an experience! If you need to unwind and let go of the crazy world, look no further. Jen is an excellent host and her getaway will remain at the top of my list.

Robins Nest
A gem of a place not too far from lots of wineries, restaurants, and more. The house was clean and spacious. Ample heating/AC as needed.

The willow tree house
This is the third time we stayed at this place. Everything was great as always. This time the house decorations were updated for Christmas which felt very festive. We chose here when visiting the Shenandoah area, close to the park and Massanautten ski resort. This time we found a great taco place close by!

Lost River Dog/Bike friendly 3BR/2BA-large deck
Beautiful location and very cozy. This is our third time staying here. We love it

Lockley Cottage at Historic Perry Farm
This was our second stay here. Very lovely cottage, nicely decorated, and is exactly as described in the listing.

Amy's Place
This is our second stay at Amy’s place. Accommodations are very nice and comfortable. Love the privacy and being able to get away from the hustle and bustle of everyday life. Very close to many hiking areas. Looking forward to staying at Amy’s place again.
Private cottage rentals

Charming riverside cottage-firepit, yard, Pets
This home is in a great location, beautiful spot on the water, nearby park. The host was responsive and flexible with our check-out. The home is clean and has all the needed amenities. We will definitely book again for our trips to Bridgewater.

Shenandoah Skyline Dr/Massanutten/Park/Trails/Wine
Had a great time. The location was so beautiful. It truly was like a vacation away from the world's busyness to just enjoy nature and a more peaceful cozy version of life. Everywhere we went around the location was super friendly and connected to nature, and the food in the vicinity was amazing. 100% recommend!

Purple Kangaroo Cottages
We had a lovely stay at this cottage. Very clean and nice amenities. 25 minutes from White tail and 15 minutes from downtown Mercersburg. Super friendly hosts.

Spectacular Mountain Retreat
This place was perfect for our weekend getaway. The cabin was spacious, clean and comfortable, plus close to so many hikes in Shenandoah national park. The hosts really thought of everything, from coffee to cookware and even having the fire pit filled with brush so we could easily have a fire. The location is nestled in the mountainside and is SO quiet, coffee overlooking the mountains and hills with nothing but the sounds of nature was therapeutic. We are already talking about planning our next trip back!

NEW * The Getaway Cottage at Rocky Marsh Farm
Another perfect stay at my favorite home away from home! Everything was immaculate and amazing as always, but Zeb went above and beyond for us when strong thunderstorms knocked down a pretty large tree on the property. It fell across the driveway, and I texted to Zeb to notify him; he responded in less than two minutes and was at the house to cut and remove the tree within 30 minutes. AMAZING guest support!

Sweet Scenes Cottage
Valerie’s place was a great getaway and they were great hosts! Very peaceful and on the river. The house was very cozy and filled with board games to play at night. 10/10

Wheatland Spring Farm + Brewery Cottage House
I recently had the pleasure of staying at an Airbnb located at Wheatland Farm and Brewery, and it was an unforgettable experience! The setting was absolutely picturesque, with sprawling fields and a charming rustic ambiance that made us feel right at home. The accommodations were comfortable and well-appointed, featuring all the amenities we could ask for. The cozy farmhouse vibe made it the perfect retreat from city life.

Milton Valley Cottage on Historic Estate Farm
We thoroughly enjoyed the cottage. My husband and I came up for a funeral and stayed in Kelly and Diane’s cottage. It was so charming and we loved seeing all the little critters around the property and visiting the cows! It gave us a homey feel in a time of sorrow. When we come back to visit family again we will definitely stay here again!
Destinations to explore
- Rappahannock River Vacation rentals
- Outer Banks Vacation rentals
- Washington Vacation rentals
- Pocono Mountains Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- Hudson Valley Vacation rentals
- East River Vacation rentals
- Plainview Vacation rentals
- Long Island Vacation rentals
- Cottage rentals Southern United States
- Cottage rentals Virginia
- Cottage rentals Maryland
- Rentals with a washer and dryer Winchester
- Rentals with outdoor seating Winchester
- Pet-friendly rentals Winchester
- Rentals with a patio Winchester
- House rentals Winchester
- Condo rentals Winchester
- Family-friendly rentals Winchester
- Cabin rentals Winchester
- Apartment rentals Winchester
- Monthly Rentals Winchester
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes