Pet-friendly vacation rentals in Winchester

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Popular amenities for Winchester pet-friendly home rentals

Pet-friendly house rentals

Guest favorite

Home in Gettysburg

5 out of 5 average rating, 96 reviews

*Dog Friendly* Minutes to Liberty Mtn & Gettysburg

ChrisRating, 5 stars6 days ago
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.
Guest favorite

Home in Downtown Frederick

4.92 out of 5 average rating, 135 reviews

Beautiful 3 BR historic home in downtown Frederick

GregoryRating, 5 stars2 days ago
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!
Guest favorite

Home in Washington

4.98 out of 5 average rating, 162 reviews

Across INN Entire Colonial HOUSE 3 Beds+Fast Wi-Fi

MargaretRating, 5 stars3 weeks ago
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.
Guest favorite

Home in Hedgesville

4.92 out of 5 average rating, 284 reviews

Round Mountn Top House! Prof. Cleaned w EV-chrger

SarahRating, 5 stars1 month ago
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!
Guest favorite

Home in Castleton

4.94 out of 5 average rating, 108 reviews

Romantic Cottage with Private Hot Tub

AkshayRating, 5 stars3 weeks ago
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!
Guest favorite

Home in Downtown Frederick

5 out of 5 average rating, 103 reviews

Sunshine House -Cheerful 2BR/2.5Bath Detached Home

KristinRating, 5 stars1 month ago
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.
Guest favorite

Home in Martinsburg

4.82 out of 5 average rating, 119 reviews

Sunrise on the Potomac near Shepherdstown, WV

JackRating, 5 stars4 weeks ago
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!
Guest favorite

Home in Harrisonburg

4.94 out of 5 average rating, 350 reviews

The Homeplace - Private House with Backyard

JamesRating, 5 stars1 week ago
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

Superhost

Cabin in Berkeley Springs

4.91 out of 5 average rating, 109 reviews

Pet/Family Friendly, Hot Tub, Large Deck

JoanneRating, 5 stars1 month ago
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 favorite

Guest suite in Myersville

4.92 out of 5 average rating, 306 reviews

Harmony Lodge nestled in wooded tranquility!

ChrisRating, 5 stars1 month ago
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!!
Superhost

Home in Rockingham

4.78 out of 5 average rating, 257 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

NicoleRating, 5 stars1 month ago
We had a great stay in Harrisonburg! The house was very clean and spacious and the pool was amazing. We will definitely be returning!
Superhost

Cabin in Hedgesville

4.94 out of 5 average rating, 111 reviews

NEW! Boutique-Chic w/fireplace @ The Woods

Ellen (Nellie)Rating, 5 stars3 months ago
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!
Guest favorite

Cabin in Delaplane

5 out of 5 average rating, 137 reviews

Herb Cottage-Elegant Cabin plus Optional Farm Tour

WilsonRating, 5 stars1 month ago
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.
Superhost

Condo in West Springfield

4.84 out of 5 average rating, 181 reviews

Beautiful 2BR/1BA Renovated Condo near DC

CorbinRating, 5 stars2 weeks ago
No issues clean quiet and convenient 5 out of 5 stars
Guest favorite

Villa in Luray

5 out of 5 average rating, 37 reviews

Private Indoor Pool~WiFi~ Arcade~Fire Pit~Views

JakeRating, 5 stars3 weeks ago
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!
Superhost

Chalet in McGaheysville

4.78 out of 5 average rating, 107 reviews

Tree top home in Massanutten next to tubing

RachelRating, 5 stars1 month ago
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

Guest favorite

Cabin in Linden

4.87 out of 5 average rating, 97 reviews

Skyland Hideaway | Mountain Cabin w/ Hot Tub

TammyRating, 5 stars3 weeks ago
We appreciated the well stocked kitchen, beautiful holiday decor and comfortable beds. Enjoyed the hot tub too.
Superhost

Villa in Orange

5 out of 5 average rating, 53 reviews

Luxurious Stay for 2 at Historic Estate

KevinRating, 5 stars3 weeks ago
Great getaway location with beautiful views and plenty of space to enjoy and relax for a few days.
Guest favorite

Guest suite in Edinburg

4.99 out of 5 average rating, 423 reviews

Garage Apartment, King Bed, Easy access to I-81

Martha HaynesRating, 5 stars3 weeks ago
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!
Guest favorite

Home in Downtown Frederick

4.85 out of 5 average rating, 96 reviews

Renovated tech-house in historic downtown

LukeRating, 5 stars4 weeks ago
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.
Superhost

Home in Manassas

4.77 out of 5 average rating, 22 reviews

Cozy Cottage with spacious fenced in yard!

CrystalRating, 5 stars2 weeks ago
Literally only need your toiletries. House has everything else. Driveway parking. Nice location. Responsive and friendly host.
Guest favorite

Cabin in New Market

4.93 out of 5 average rating, 161 reviews

The BlackPearl•Secluded•Hot tub 1.5 hs from DC

MaiRating, 5 stars3 weeks ago
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.
Superhost

Bungalow in Front Royal

4.93 out of 5 average rating, 76 reviews

The Pond Cottage- Fantasy Getaway with a Waterfall

JoshuaRating, 5 stars1 month ago
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.
Guest favorite

Home in McGaheysville

5 out of 5 average rating, 39 reviews

Pet-Friendly 4BR in Ideal Location @ Massanutten

WendyRating, 5 stars1 week ago
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

Destinations to explore