Pet-friendly holiday rentals in Winchester

Great place to stay for the night! Kitchen was stocked with everything you could possibly need! The Mountain View from the balcony was amazing! Rob and Max were great hosts!

We had a wonderful time at "The Burrow"; one of our best experiences with an Airbnb yet. The accommodations were top notch and our host's hospitality was above and beyond. The wrap around porch was our favorite place to relax at any time of day, with spectacular views . We enjoyed an evening next to the firepit with plenty of wood to burn. All in all it was a great experience and we would come back in a heartbeat!

This place is AMAZING! So many fun things to do! The hot tub in the cave was mind blowing, we loved it! Our 6yr old enjoyed feeding and petting the bunnies and chickens! Fishing was so much fun! Ken was an amazing host and responded very quickly! !!5 STARS!! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

Really beautiful place with lots of character! So peaceful and amazing views!! We loved it. :). Thanks Julie!

I’m pretty sad that I don’t own this house. Pictures don’t it justice, and the pics are incredible. The house, the cows, the coziness….I’ve already shared this house to a few friends! Kayla was very responsive throughout our stay. 5 stars all around!

Very peaceful, a place to get away and relax. Restful. Grounds are well cared for.

I was looking for a quiet place with a beautiful view to get away and have a kind of retreat. Alan's place was just the ticket. Got in some hikes and some quiet sitting. Grilling for dinner and watching the sky out over the valley was a real treat.

Kae is an A+ host!! Absolutely wonderful home and she is always very responsive and sincere. We have stayed several times over the last couple years. Excellent every single time!!

Peaceful and perfect little getaway! Stephen’s cabin in the woods was quiet, cozy, and surrounded by nature.. Thanks for the awesome stay!”

We loved our time at this peaceful property. It was nice to wake up and hear the farm animals nearby. My son loved being able to play basketball and use the pool. Everything was clean and comfortable. Thank you!

Teddi and Adam were great hosts and have such a beautiful place that provided some much needed peace and quiet! We really enjoyed our stay!

Lynn's place was excellent! Everything was perfect, really. We felt so comfortable and well cared for from the moment we walked in to the moment we left. All of the amenities are A+. The furniture is luxurious and tasteful. We would return without hesitation if we ever find ourselves out that way again. Heather

We really enjoyed our stay here. The house offered so many things for us to do as a family. We had such a good time playing darts, pingpong, board games, and hanging out around the fire pit. The Woods is our favorite place to go because of all the amenities. Highly recommend!

This is a lovely and homey cottage. Very beautiful courtyard, backyard and pool area. The hosts were friendly and very helpful with suggestions when our original excursion was cancelled. The kitchen was very nicely stocked and had everything we needed. The beds are very firm.

Looking forward to staying here again. I'd highly recommend for couples, families, friends and solo.

Omg ! we had an amazing time it was so beautiful and they took amazing care of us! will be visiting here again no doubt

Rachel’s place was just as described. It was a peaceful place but not too remote as you could reach stores and such within 15 min. Rachel gave great directions and had terrific communication. Space was clean and tidy.

We had a wonderful stay at the cabin! This property was incredible, so beautiful and peaceful. The cabin itself is very cool and in great condition albeit rustic. The only shower is an outdoor shower, which was warm and serene. That’s the kind of unique quirk of rental that makes the experience extra memorable. There are tons of sitting areas outside from the swing on the covered porch to the area around the sunken fire pit, all which overlook the large field on the property and the horse field at the adjacent property. Another perk was that it was dog-friendly as we had our two dogs with us, who loved the property as well. Overall, such a great experience at Judith’s place and I recommend to anyone coming into the area who is looking to disconnect and relax!

The home was in a private peaceful area . We thoroughly enjoyed the big yard and the two swings for taking the beautiful scenery in. We relaxed by the fire pit and loved the lit up pathway walking out to it . The two person shower was a treat. It really was pretty. After we came back from dinner we played some pool in the game room and educated my sons on the record player which delightfully brought us back in time. One night here was not enough to enjoy all this lovely home has to offer. Highly recommend staying a few days when you come!

Absolutely loved this little getaway for my husbands birthday! It was so quiet and peaceful but had everything we needed. The design was so well thought out and absolutely beautiful. Reagan was amazing with recommendations and so quick to respond - I cannot wait to come back to the Treehouse! I wish I could have stayed longer.

Beautiful farm cabin, huge property to walk around, all amenities needed for a relaxing weekend, and probably the cleanest Airbnb I’ve ever walked into … Definitely recommend.

We had an amazing girls' weekend! The house was cozy, spotless and perfect for our group. Dolly & Brendan were super responsive and gave us terrific recommendations for local restaurants and wineries - everything we tried was a hit. We loved being able to sit outside and unwind by the firepit. Would definitely stay here again!

This property was so beautiful and such a relaxing stay! Robert was extremely thorough and there was not a single hiccup in the process! The house was spotless and was soo beautifully decorated! It was even more perfect than the photos portray. They did a truly phenomenal job with the place. Everything was in working order and there was plenty of supplies on hand. I also greatly appreciate the level of cleanliness in this property. It stood out as well! I hope we get the chance to return here again soon!

The home is exactly as described, spacious and comfortable, accommodating 5 people with plenty of space to spare. It features great furniture, a deck, BBQ, and hot tub. Overall, highly recommend and will be returning again. Matt is a great host and very responsive.