Pet-friendly vacation rentals in Winchester
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Top-rated pet-friendly home rentals in Winchester
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Pet-friendly house rentals
Home in Gettysburg
5 out of 5 average rating, 96 reviews*Dog Friendly* Minutes to Liberty Mtn & Gettysburg
My friends and I planned our first "Friendsmas" get together and the experience was fantastic. The house was very nice and the hosts went above and beyond to ensure we had a nice stay. All the necessities were available that you'd expect, plus some extra bonuses. A coffee bar with k cups and various selections of flavored syrup to use was available. Once you entered the dining room, a gift basket with a variety of snacks and a welcome message written on a board. All the linens were clean and pristine. Also, there were plenty of towels to accommodate our needs. Wood was made available if we wished to have a campfire one night, which we didn't because we didn't have enough time. The impression on me and my friends has us considering this place as a yearly "Friendsmas" tradition going forward. Thank you for the high-quality hospitality.
Home in Downtown Frederick
4.92 out of 5 average rating, 135 reviewsBeautiful 3 BR historic home in downtown Frederick
beautiful spot, centrally located to everything. walking distance to restaurants and bars but far enough to be quiet and comfy. Highly recommend this place and the host was fantastic!
Home in Washington
4.98 out of 5 average rating, 162 reviewsAcross INN Entire Colonial HOUSE 3 Beds+Fast Wi-Fi
We had a wonderful stay for my birthday weekend. The home was clean and very spacious. We were able to walk to dinner and breakfast and it was a beautiful little town.
Home in Hedgesville
4.92 out of 5 average rating, 284 reviewsRound Mountn Top House! Prof. Cleaned w EV-chrger
Had a great stay with our two dogs! We enjoyed relaxing on the deck and exploring the nearby trails. Talk about a peaceful location - Area was private and had a great view. Be sure to check out the sunrise through the panoramic windows! We also packed some food and found all necessary utensils and cookware available. Thanks for letting us stay at your lovely home!
Home in Castleton
4.94 out of 5 average rating, 108 reviewsRomantic Cottage with Private Hot Tub
This is a beautiful property, calm and serene. Great for a weekend getaway in the DC area. We loved the private hot tub and the fireplace! The cottage was clean and cozy, made us feel at home!
Home in Downtown Frederick
5 out of 5 average rating, 103 reviewsSunshine House -Cheerful 2BR/2.5Bath Detached Home
Our stay at Kaylin & Alex's was fabulous. The house was very clean, beautifully decorated and had all of the little extras. We brought our pups so it was great to have a yard and park close by. We could tell from the photos that it would be helpful to bring a gate to fence off an open part in the yard. Location was very walkable and the driveway was a perk. We love Frederick and would love to stay at Kaylin & Alex's house again.
Home in Martinsburg
4.82 out of 5 average rating, 119 reviewsSunrise on the Potomac near Shepherdstown, WV
A few friends stayed at Tony's place for the JFK 50 race weekend. This was a terrific home base. Beautiful views of the river and the hot tub was a terrific perk for our sore legs!
Home in Harrisonburg
4.94 out of 5 average rating, 350 reviewsThe Homeplace - Private House with Backyard
The house was such a nice peaceful place to unwind. It was an easy drive from JMU to visit our daughter and to go to campus. Rooms were comfortable, and the house had everything we needed. Would love to stay again if we were in the area.
Pet-friendly home rentals with a pool
Cabin in Berkeley Springs
4.91 out of 5 average rating, 109 reviewsPet/Family Friendly, Hot Tub, Large Deck
I rented Connors cabin for 7 friends and we had a relaxing fun weekend. We watched the birds and chipmunks from the living room. We got in the hot tub and went to the indoor community pool which was a nice bonus. Downtown Berkley springs is a hop, skip, and jump away. Bring water jugs to get water from the natural spring.
Guest suite in Myersville
4.92 out of 5 average rating, 306 reviewsHarmony Lodge nestled in wooded tranquility!
We had a wonderful trip and Elisa’s place was fantastic! Lots of nice small touches. Wonderful location, lots of great hiking, and she provided several excellent recommendations for places to eat. Definitely recommend it would stay again!!
Home in Rockingham
4.78 out of 5 average rating, 257 reviewsStone Spring - Heated Salt Pool - on 2.5 Acres
We had a great stay in Harrisonburg! The house was very clean and spacious and the pool was amazing. We will definitely be returning!
Cabin in Hedgesville
4.94 out of 5 average rating, 111 reviewsNEW! Boutique-Chic w/fireplace @ The Woods
This house came highly recommended by my daughter, and I understand why. Honey House was even more than I expected. The best part of the house? The screened-in porch at the back. If you enjoy being surrounded by nature and having a quiet spot to read, relax, and simply absorb the peace, you will love this feature of the house! I loved the decor throughout, the comfort, and the way everything was labeled to ensure ease of use. How cool that there is a huge vinyl collection and a vintage turntable on which to play it! I greatly respect that the owners share that wonderful addition to the experience. The area is beautiful, there is much to do in the surrounding towns, and the people are terrific. Explore what the area has to offer---you will be glad you did. Thanks for a relaxing stay!
Cabin in Delaplane
5 out of 5 average rating, 137 reviewsHerb Cottage-Elegant Cabin plus Optional Farm Tour
I planned to propose to my girlfriend over a romantic farm and Shenandoah getaway weekend. Andrea was very excited and helped make the weekend really special. The grounds were amazing and so beautiful with trails to take walks on and many animals to see. We brought our puppy and we had plenty of space to safely let him off leash to run around. He had as much fun as we did (and we got engaged!) Her restaurant recommendations were spot on, so definitely give those a try. We did the farm tour on the last day, and it was so personal, interactive and informative. Do not skip the tour!!! Andrea was so kind and generous with us. We cannot recommend this place highly enough.
Condo in West Springfield
4.84 out of 5 average rating, 181 reviewsBeautiful 2BR/1BA Renovated Condo near DC
No issues clean quiet and convenient 5 out of 5 stars
Villa in Luray
5 out of 5 average rating, 37 reviewsPrivate Indoor Pool~WiFi~ Arcade~Fire Pit~Views
Can not say enough great things about this spot. Beautiful location, sparkling clean, amazing indoor pool, lots of fun games to play, great outdoor hangout spaces, and more… Would definitely recommend and will probably be back again sometime. Thannk you very much!
Chalet in McGaheysville
4.78 out of 5 average rating, 107 reviewsTree top home in Massanutten next to tubing
We really enjoyed our stay in Massanutten, and our lodging contributed to our great trip. The condo was spacious, well furnished and had everything we needed for our stay. Mary and Chris were proactive and communicated instructions clearly when it came to check-in/check-out, specifics about the unit itself, etc. The unit was a good value We would absolutely stay here again!
Private, pet-friendly home rentals
Cabin in Linden
4.87 out of 5 average rating, 97 reviewsSkyland Hideaway | Mountain Cabin w/ Hot Tub
We appreciated the well stocked kitchen, beautiful holiday decor and comfortable beds. Enjoyed the hot tub too.
Villa in Orange
5 out of 5 average rating, 53 reviewsLuxurious Stay for 2 at Historic Estate
Great getaway location with beautiful views and plenty of space to enjoy and relax for a few days.
Guest suite in Edinburg
4.99 out of 5 average rating, 423 reviewsGarage Apartment, King Bed, Easy access to I-81
I adored staying there. The space was incredibly cozy and I loved how everything was decorated. The beds were all comfortable. And the sofa area was cozy too. I liked that it had its own key and how complete the kitchen felt. I would definitely want to stay again!
Home in Downtown Frederick
4.85 out of 5 average rating, 96 reviewsRenovated tech-house in historic downtown
Very cozy BnB in historical district. Right down the road from restraunts. We were able to walk to our rehearsal dinner. Beds and furniture were very comfy. Would definitely stay again if were in the area.
Home in Manassas
4.77 out of 5 average rating, 22 reviewsCozy Cottage with spacious fenced in yard!
Literally only need your toiletries. House has everything else. Driveway parking. Nice location. Responsive and friendly host.
Cabin in New Market
4.93 out of 5 average rating, 161 reviewsThe BlackPearl•Secluded•Hot tub 1.5 hs from DC
We loved our stay. The cabin is in a nice secluded area. Communication with Bobby was smooth and he agreed to accommodate a last minute request. We especially loved the hot tub and how private it was despite being outside. Thanks for having us.
Bungalow in Front Royal
4.93 out of 5 average rating, 76 reviewsThe Pond Cottage- Fantasy Getaway with a Waterfall
The place was fantastic! even though we were close to the trails/national park, we ended up spending most of the time on the property with our dogs. There was an insane amount of space for them to run around/enjoy themselves. The views are great, the house was clean and had everything you needed for a nice little get away. Definitely considering coming back.
Home in McGaheysville
5 out of 5 average rating, 39 reviewsPet-Friendly 4BR in Ideal Location @ Massanutten
Lovely home in Massanutten! David responded immediately when there was any communication sent. Beds were comfortable but very firm. We booked for our daughter’s college graduation, and need a lot of room. The pool table was great for our younger sons to have something to do.
Quick stats about vacation rentals that are pet-friendly in Winchester
Total rentals
30 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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