
Pet-friendly holiday rentals in Chesterfield
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Top-rated pet-friendly home rentals in Chesterfield
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Pet-friendly house rentals

Fox Hollow on Sentinel
Our second stay at Fox Hollow. Great location next to town. Beds and baths worked well for us. Access to trails and sledding out the back of the property was great. The front porch puts you in a special place and mood. J

Large New England Home w/ Gorgeous Mountain Views
This is a great house to stay in. There's a lot of space, places to sleep, sit and relax, eat, watch tv, play games, work, read, cook. Plenty of hot water.. Very private, although in a neighborhood. Nice back yard area when not covered in snow, looking up at the mountains behind. Sheri is top notch. Easy to reach, super friendly and helpful, easy going. We came at the tail end of a snow storm, but the driveway was cleared enough to get our car in and then Sheri worked with us to make sure everything was cleared before we had to go out the next day. Easy walk into the cute town of Bristol. Handful of nice shops (books, games, art, crafts, gifts, toys) and restaurants: Wokky's--ok Chinese/great staff; Minifactory--out of sight coffee/biscuits/sandwiches/fresh ingredients/lot of gluten free; Cubber's--locals' joint/excellent pizza/sandwiches; Farmhouse Chocolates--superb fresh organic truffles, bars, caramels/chocolatier is wonderful. Easy drive to Mad River Glen, Sugarbush for skiing.

Birchwood Lodge - Our Home in the Woods
Our first time at Lynda's home in the woods. Place was exactly how described! Was very cozy and we had everything we needed for our stay. Great location, very private and close to skiing and town. We enjoyed to sauna every day. We got to relax and really enjoy ourselves. Lynda was very quickly to respond and was very friendly and helpful. I would definitely plan to go back, we loved it!

Mid century modern gem with views of Sugarbush
Place was as advertised. Beautiful, great location, great views, close to convenient grocery shopping and slopes. We'd love to come back some day.

Gorgeous 1835 Farmhouse w. Lake/MTN Views!
It is a beautiful house where you can smell the family and we liked that a lot. It is close to the ski slopes, very clean and comfortable. Lidsa and Tom have very good communication, excellent service.

Ten Springs Farm at the foot of Mt. Mansfield
One of the BEST AirBnB stays we have ever had! The house and grounds are perfect for a VT getaway. It was the ideal home base for our adventures to Ben & Jerry's, Stowe, Woodstock, Middlebury, Burlington, and Hanover, NH. Jericho Market is only a few minutes away and has all the groceries you need (I seriously love the grocery store). Our favorite Maple Syrup experience was with the wonderful folks at Palmer Lane Maple in Jericho. Bob was wonderful to work with. I cannot recommend this house enough! Internet, hot water, space, privacy, kitchen tools, etc. were all perfect. We had an excellent time and would go back in a heartbeat. All four of us truly felt right at home.

Sweet Blue Mint Ski House
This is our second stay here. The house is roomy and clean. We even had a visit from the neighborhood bear!!! Location is perfect and private. I highly recommend.

Rand’s Retreat
We had a great stay! Loved playing board games in front of the fireplace. The house is minutes to Brandon (an adorable town) but still feels away from it all.
Pet-friendly home rentals with a pool

Upper Yurt Stay on VT Homestead
I needed a little break from my every day Vermont life. This was the perfect spot to get away from everything, but still not be far from home. I would definitely go back! Thank you so much!

Lodge At Spruce Peak Alpine Studio Pool / Mt Views
PERFECT winter getaway! The location was amazing…our room had a wonderful view of the mountain, pool and hot tub. The resort itself was beautiful-great staff! Nice shops, excellent dining and bars! And, of course-snowboarding! Will definitely return! Can’t say enough about Stowe Mountain Resort! AWESOME!

Apartment, comfy and cozy with kitchen/gas fire
Rebecca’s air bnb is awesome in a great location and she truly goes the extra mile for her visitors.

Cute Cottage - Poolside - Minutes To Activities
Linda was a fantastic host, and her home was even better than listed. The cabin was a good size for our family of four + dog; the 2 bed / 2 bath arrangement allowed for good privacy when needed. The fireplace was great for apres and winding down at night. Location is a nice mix of seclusion (off the Mountain Rd), but close to everything.

EPIC Stowe Getaway - Great For Families & Friends
We had an amazing stay, this trip far exceeded our expectations and staying in such a nice place made everything so much more enjoyable. This spot was the perfect mix of private and secluded while still also being very close to Stowe, and Johnson. We were able to complete everything on our itinerary while also being able to come back every night to a beautiful home with everything we needed. It was very nice to be able to sit down with family we havent seen in so long and enjoy an amazing home cooked meal or play some board games. Thank you Kristin for your amazing hospitality. This has made Vermont one our favorite states to visit. We will definitely be back.

Large Cozy Lodge Near Whiteface w/ Hottub & Sauna
House was beautiful! Easy check in and they let us check in early :) check out instructions were very clear and not overwhelming

In Resort 5* Smuggs Pass/Camp inc Mt View Nr lift!
No frills but that’s what we were looking for, for a quick spring ski trip! Affordable and great for the kids with a ton to do on the property. Game space, pool, hot tub, laser tag plus skiing! Super fun packed few days. Host very communicative. We will return.

Château Chavís
Fantastic place in the country. We were looking for a quiet place in the country, where we could relax with our dog for a short weekend place - and Travis' place ended up being the perfect place for that. The house has everything you need for a break, Travis was very responsive and proactive, and the fenced in yard was large (our St Bernard really appreciated that)! In addition to the fenced in yard, there is also a trail running through the property alongside the stream. Good location in the mountains - private and rural but also a short drive away from amenities.
Private, pet-friendly home rentals

Cozy cottage in peaceful location
We had such a fun trip! Nikki’s cottage was absolutely gorgeous, nestled in the countryside. Would absolutely stay here again!

Charming getaway tucked away in the Green Mtns
We appreciated how pet friendly this place was! Fenced in yard. Blankets to cover the furniture to allow dogs on them. Close enough to many different ski mountains. Perfect to come home to the wood stove and hot tub.

Cozy 2 bedroom true log cabin
I wish I could rate this home 6 stars. It is beautiful, peaceful, private, and surrounded by nature. The two bedrooms are great and very comfortable, and they actually have anything you might need in terms of toiletries. Corey was super responsive and helpful, he quickly answered the few questions that I had. Would absolutely recommend this home to anyone looking for a small getaway.

1 Acre Private Island Cottage (Sat Check In/Out)
This is the fourth year we have booked Dogatraz island and look forward to it every time. Nick, the property manager is responsive, on time and super helpful. We love the private island and being able to let our dogs run free, especially our deaf dog. She always has to be on a leash where we live and being able to watch her run is priceless. Both pups love the kayak and the water (but neither will swim-LOL). I love the idea of no Wifi and forcing us to detach from our otherwise busy lives. Looking forward to next year!!

Sunset Getaway ~ Private Beach | Hot Tub
Exactly as described in advertisement with the exception of the view from the front balcony and living room -- it is BETTER than described and expected! This a repeat for the future.

Pet Friendly Rental Unit
We had an amazing stay! The location was perfect for our ski trip, and the place was exactly as described: spacious and comfortable for our group. One of the highlights was catching the northern lights, thanks to a thoughtful reminder from our host, Shelly. She was super responsive and friendly. Would definitely stay here again!

Whiteface View Retreat STR # -200022
We had a wonderful stay. The apartment was perfect for 4 people and a dog for a weekend trip. Having a place right down the stairs to take the dog to use the bathroom made it much more convenient than a hotel. We spent most our weekend outside or exploring downtown Lake Placid which was just a few minutes away so the location was perfect. The apartment was clean and well maintained.

Beautiful 1 Bedroom Suite with private entrance
A short stay while in town with my dogs here was perfect. The apartment was perfect, clean & quiet. Christine had some great trail recommendations for me and the pups between meetings. The WiFi and work stage were perfect too.
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- Sugarbush Resort
- Smugglers' Notch Resort
- Spruce Peak
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Cochran's Ski Area
- Ethan Allen Homestead Museum
- Parc Safari
- Fort Ticonderoga
- Country Club of Vermont
- Cozy Cottages & Otter Valley Winery
- Vermont National Country Club
- Autumn Mountain Winery
- Lincoln Peak Vineyard
- Leahy Center for Lake Champlain
- Burlington Country Club