
Pet-friendly holiday rentals in Windsor County
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Top-rated pet-friendly home rentals in Windsor County
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Pet-friendly house rentals

Beautiful Historic 1909 Library with a Fireplace
We love the library! Stayed here 4 times now. It's a special place filled with history, in a beautiful area with quite a bit to do nearby. The fireplace is lovely and cozy, the bed is super comfortable, the kitchenette has everything you need, and we love that it's dog friendly too. There were even some toys for our pup to enjoy during our stay. Highly recommend for a unique and special getaway!

The Olde Norwich Cape
The house was perfect for our needs. There are 8 single beds with several hang out spaces. the kitchen was well stocked and the place was clean and comfortable.

Modern Farmhouse on 25 Acres - Superb Views
We had a quiet stay at the Farmhouse. Very peaceful and quiet location. Lots of space for our dog to roam. The house is very nice and clean. We enjoyed having coffee and looking out across the fields, reading, and cooking. It’s near the small village of Rochester with a few restaurants and otherwise we explored neighboring towns like Middlebury, Waitsfield, Stowe, and Montpelier.

Modern 3-bedroom A-frame in Londonderry w/ Pond
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

The McKinley House
We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!

Blueberry Hill Escape | Pet Friendly | HotTub | Fi
We enjoyed our time at Chris's house. The house has everything you will need including coffee and kcups. We enjoyed the fireplace in the living room and the hot tub. The view from the hot tub was great! We didnt get to use the fire pit because it was raining the whole time but it looks like an awesome hang out area. Communication with Chris was great. We recommend a stay here and would definitely return in the future!

Mountain Home ready for you!
This place was great. Very spacious and comfortable with beautiful views and sunsets! 10/10

Greystone 1830
Very special place - we loved it and hope to come back soon! It is everything wonderful about a stone home with a modernized kitchen and living areas. So cozy and beautiful!
Pet-friendly home rentals with a pool

Dog-Friendly Mtn Escape/AC/Pool/
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

Ranch at Mendon Mt Orchards
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

SugarBear- Pool, AC, Sauna, Gym, Tennis!
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

Charming Killington get away with pool, sleeps 4
Great place to stay for the weekend! Super close to Pico and Kilington mountains. Would highly recommend!

Farmhouse, Fireplace & Office | Wheelock Hideaway
Very quiet and cozy. Comfortable beds. Lots of room for everyone.

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.

Elegance Meets Rustic Charm: Vermont 3-Bed Retreat
Our stay was a family group of six adults and my two grandchildren who are ages seven and eight. We decided to spend the week in Queechee with the second weekend being a family wedding. We loved the peace and comfort of a private home and especially enjoyed the backyard deck playing cornhole and barbecuing. Being tucked away up off of Willard Road was worth the very slight inconvenience of an extra five minutes or so drive to get back into Queechee proper. The owners were very responsive to any concerns or questions I had about the property during our stay. The home is spacious and lovely with attractive and comfortable furnishings. The kitchen is open to the main level and very well equipped for cooking all your meals if you choose. our granddaughters enjoyed the games that are stashed away in the front closet Highly recommended!

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!
Nice place for the 6 of us and dog for a long ski weekend in March. Condo was as described. The kitchen was very clean, nothing in fridge. New fridge and new oven. The bathrooms were very clean. The beds were comfortable. The upstairs space a bit tight for 4 adults, but we managed fine. Two of the twin beds are in an open loft area, which didn’t bother us as we were all going to bed at the same time and waking early to go skiing. Just mentioning this in case you were looking for a 3rd bedroom that was fully enclosed. The Spa and Cafe/ Wine Bar were a great addition to our ski weekend activities. The host was wonderful and very responsive. We highly recommend this condo.
Private, pet-friendly home rentals

~The ClubHaus~
The Clubhaus was the perfect private getaway my girls and I were looking for. The area was secluded and beautiful, but not too far from local favorites that we felt out of the way. It was the most relaxing and homey place I’ve stayed to date- I can’t wait to come back and enjoy the serenity again!

"Swiss Charm"- A Beautiful Riverfront Chalet
We had a lovely stay at James’ chalet. Located near skiing, and on trails for snowshoeing, it is ideal. The kitchen is well stocked, the beds are very comfy, and a strong internet for work needs. The cozy wood burning stove, and the bubble tub were welcome after a cold day on the slopes. James was very responsive and a perfect host. I would love to return and make good use of the grill and fire pit in the spring!

Riverside Cottage - Bridgewater Vermont
Absolutely loved every minute spent here. We had plans for a lot of nearby activities, but the property was so stunning we decided to enjoy it and stayed home. We cooked, had tea by the river, played games and engaged in deep conversations. There were awesome restaurants within 30 mins of driving. We bathed in the river, played in water quite a bit. Linda and Chris were supportive, very responsive and always there for us. Thank you for sharing this stunning property with us. I hope you be back. We were a group of 3 - and we were welcomed with a cute hamper and lots of warmth. Don’t miss the game room - which has a separate entrance from the main house.

Fairlee Log Cabin
I was so happy staying at Brooke's cabin. There was so much to be happy with, I'll do my best to list them all! 1. Brooke was well responsive - I ran into 2 small problems and she was proactive and fixed them fast. 2. The whole place is super dog friendly! I am often worried where my dog is and isn't allowed in Airbnbs, not here! Brooke even left out dog toys, bowls,and beds as well! 3. All linens were cleaned, even the throw blankets! 4. the trail in the backyard is a nice touch! unfortunately I didn't have many non rainy days so only got to explore some of it, but it is a different world back there! 5. The kitchen is incredible: 3 different ways to make coffee along with a frother and a grinder! the pots and pans are chef's choice! and the knives aren't dull! I was well equipped to cook and theres plenty of space to do so. 6. the bathtub is a godsend! 7. incredible library! I cannot recommend this place enough!

Hancock hideaway
Heidi's place is a wonderful cabin in the woods with all you need to enjoy the nature in Vermont. Super peaceful and the property is well maintained. I would highly recommend staying here to enjoy your vacation!

Vermont Chalet
Had a great time at Janie’s chalet. It was peaceful and quiet. Janie was a great host and very attentive.

Private Log Cabin near Quechee
Halley was very accommodating and kind! She has a list of things to do and places to eat on her fridge. The surrounding area is serene and it was such a nice escape!

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way
I was fortunate enough to spend a very life changing trip here. Words can’t express my gratitude.❤️🥹🙏
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Autumn Mountain Winery
- Fort Ticonderoga
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Northeast Slopes Ski Tow
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Hooper Golf Course
- Brattleboro Ski Hill
- Bretwood Golf Course
- Fox Run Golf Club
- Ekwanok Country Club
- Veterans Memorial Recreation Area Ski Hill
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