
Pet-friendly holiday rentals in West Windsor
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Top-rated pet-friendly home rentals in West Windsor
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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!

Hideaway Cottages, Cottage A
We have been visiting the New London/Sunapee area for years. This was one of our favorite places to stay! It was so peaceful and just what we needed. It was clean, comfortable, and the perfect location. A lovely stay.

Comfortable farmhouse with stunning views
Such a cool house. We loved the charm of the older section of the house. So many private spaces to cozy up and read a book. Then there is the more modern portion of the house. It was perfect for the folks to watch tv and enjoy the VT scenery out of the large windows. The road is quiet and the area is lovely. We easily drove into Manchester for groceries and dinner. Really loved it!!

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

The Guest House at Sky Hollow
This is my second time staying at one of Jess’s properties - and I’m sure it’s not my last. The property is beautiful inside and out and has everything you need. I was in town for a full week and this place was just what I needed to relax after long work days. I can’t recommend staying at one of Jess’s places enough. You won’t regret it!!

Renovated Vermont Schoolhouse – Close to Okemo
Marianne was so responsive and kind. The place is super close to Okemo. The space is probably bigger than it looks like in the photos. Super quiet secluded spot. Kitchen was nice and big for us to cook for a troop of hungry skiers. Thought this was a really nice family oriented spot. Second time we have stayed there and hope we can come back there for more ski trips!

Lovers Honey Pond Treehouse with hot tub & sauna
Ben's place is special, relaxing and unique. Well thought out details to the cabin, even little things that give it charm. Great communicative and friendly host.
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!

Leonard’s Log - Private Hot Tub, Fire Pit, A/C
The cabin was lovely! We went for a little weekend getaway with some friends and it is a great space for such an occasion. There is a surprising amount of space in and around the house and we didn't even use the three season porch. The hosts were also very responsive and easy to communicate with. Definitely a cute little home away from home!

Beautiful rustic woods and fields retreat.
This was my third time staying on Rosalind's property, but my first time in the "retreat" unit. The space is better in person than in the photos! It's a spacious two level unit with a huge bedroom/loft type area, perfect for setting up your yoga mat! The high ceilings and large forest facing windows in the bedroom were a highlight for me. Rosalind has always been a very responsive, thoughtful, and flexible host. I can't wait to stay again!

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.

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.

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
Peaceful, Serene location just 10 minutes from Stratton. We enjoyed the use of the new hot tub, and roomy kitchen. This space is surrounded by nature with plenty of space for you and your group. Would definitely stay here again!

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
Lovely house can’t wait to rebook for next snowboard trip!
Private, pet-friendly home rentals

WildeWoods Cabin | gas fireplace, yard + gardens
Hilary’s place is the perfect place to relax or to stay with the intention of going on a hike to Mount Cardigan. It’s well equipped with everything you need for cooking, lounging and showering. And for those who don’t have dogs, don’t worry about cleanliness. I could roll around on those carpets. The bed is super soft. You sink right in. It was raining a lot the weekend I was there and I also had a zoom meeting for work so we didn’t go outside. WiFi was super fast. And honestly, it’s so cozy and clean in there, I was happy to stay in the whole weekend.

Newport Jail “Break”
Such a fun and unique place to stay. Location is great with lots of eating places in walkable distance. Would stay here again!

Scandinavian design Cabin w/ private hiking trail
Easy drive from Boston. What I loved most about the cabin is that it is cozy and had an indoor fire option. It rained all weekend, but the cabin was so cozy! We had no qualms about sitting in the hot tub under the rain, and spending the evening in front of the wood burning stove as the rain pattered on. So close to restaurants in South Royalton!

Vermont Chalet
I had a blast in the beautiful Chalet. Everything was what I was expecting and more. The review matched the property and vibes. From the beautiful views outside to the cozy vibes in the loft upstairs, it was amazing. I had a couple of questions for Jason and he answered insanely quick and was very helpful with his information. The Pac-Man was a great addition too. P.S 24,910 is my high score!! I totally recommend and might even come back some time in the future. The host, cabin, property, and area was delightful, nothing but love for this stay!!

Cozy 4-season Cabin on Pond - "East Cabin"
Exactly as advertised - beautiful, very private, clean; a perfect place for a solo/couple getaway. Seamless communication and logistics with the friendly hosts, who clearly maintain the cabin with care. Book it!

Apple Blossom Cottage: A Tiny House
I had an amazing time at your location. I was able to use it as a home base for all the different hiking trails in the area. Your property is really quiet and peaceful. I loved being able to enjoy nature and breathe in some fresh air.

Private Barn On a Hilltop in Fairlee, Vermont
Heaven on Earth does not come close to describing this property. Perfect place for city goers to escape into nature and be reminded of what serenity and peace are. We were able to see the stars at night like we never have before. My partner and I kayaked, visited Glen Falls and had a blast at Dog Mountain. Highly recommend all these activities! Visiting Chapman’s General Store (5 minutes from the property) is a must! Amy and Reg were very accommodating and communicative when we needed anything. Reg was nice enough to point out a short trail in the back of the property where our pup could play in the water a little. We were grateful for every minute spent here and the clean, respectful and inviting environment they have created for their guests.

Green Mountain Modern House: iconic modern getaway
We stayed for a few days during our April break and had a nice relaxing time. The area was quiet and the host had a ton of great recommendations in their guidebook for things to/places to eat, but a lot were closed for the off-season/the days we were there, even in nearby Manchester (that's on us, certainly no fault of the host's just something to consider when timing your stay). The house had a unique vibe that our kids especially were thrilled with – as Star Wars fans, they referred to it as the Sand Crawler House. The stream directly across the street provided a fun and peaceful attraction and the trails in nearby Jamaica State Park were beautiful as well. The home was as described, stocked with board games and puzzles, etc., and the EV charger was a nice bonus for our plug-in hybrid SUV.
Quick stats about holiday rentals that are pet-friendly in West Windsor
Total rentals
20 properties
Nightly prices starting at
$185 AUD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Monadnock State Park
- Owl's Nest Resort
- Pico Mountain Ski Resort
- Pats Peak Ski Area
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Ragged Mountain Resort
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Bretwood Golf Course
- Brattleboro Ski Hill