Pet-friendly vacation rentals in Chesterfield

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Chesterfield pet-friendly home rentals

Pet-friendly house rentals

Superhost
Home in Lake Placid
4.82 out of 5 average rating, 173 reviews

Fox Hollow on Sentinel

JohnRating, 5 stars3 months ago
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
Guest favorite
Home in Bristol
4.88 out of 5 average rating, 155 reviews

Large New England Home w/ Gorgeous Mountain Views

ChristopherRating, 5 stars2 months ago
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.
Guest favorite
Home in Wilmington
4.88 out of 5 average rating, 166 reviews

Birchwood Lodge - Our Home in the Woods

JanaRating, 5 stars1 month ago
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!
Guest favorite
Home in Waitsfield
4.96 out of 5 average rating, 163 reviews

Mid century modern gem with views of Sugarbush

PhilippeRating, 5 stars2 months ago
Place was as advertised. Beautiful, great location, great views, close to convenient grocery shopping and slopes. We'd love to come back some day.
Superhost
Home in Grand Isle
4.87 out of 5 average rating, 156 reviews

Gorgeous 1835 Farmhouse w. Lake/MTN Views!

Maria Del CarmenRating, 5 stars3 months ago
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.
Top guest favorite
Home in Underhill
5 out of 5 average rating, 103 reviews

Ten Springs Farm at the foot of Mt. Mansfield

JenniferRating, 5 stars3 months ago
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.
Guest favorite
Home in Waitsfield
4.91 out of 5 average rating, 149 reviews

Sweet Blue Mint Ski House

TommyRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Brandon
4.93 out of 5 average rating, 128 reviews

Rand’s Retreat

AnneRating, 5 stars1 month ago
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

Guest favorite
Yurt in Randolph
4.94 out of 5 average rating, 452 reviews

Upper Yurt Stay on VT Homestead

TeganRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Granville
4.96 out of 5 average rating, 141 reviews

Epic Views of the Green Mountains

StephenRating, 5 stars4 weeks ago
Great place to take your family if you like to escape from humanity! Very remote setting and plenty of places to hike. The house is as described and the kitchen if fully stocked to make full dinners. My daughters, our German Shepard and I had a wonderful time. Suggestions - bring groceries as Granville is in the middle of nowhere. Closest store is in Rochester, 12 miles South. William was very commun icative and the value for the money was phenominal. Hope I can return next year!
Guest favorite
Home in Stowe
4.88 out of 5 average rating, 257 reviews

Lodge At Spruce Peak Alpine Studio Pool / Mt Views

SevastiRating, 5 stars2 months ago
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!
Superhost
Guest suite in Jericho
4.74 out of 5 average rating, 288 reviews

Apartment, comfy and cozy with kitchen/gas fire

ZachRating, 5 stars1 month ago
Rebecca’s air bnb is awesome in a great location and she truly goes the extra mile for her visitors.
Guest favorite
Cottage in Stowe
4.77 out of 5 average rating, 240 reviews

Cute Cottage - Poolside - Minutes To Activities

ChrisRating, 5 stars1 month ago
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.
Top guest favorite
Home in Stowe
4.98 out of 5 average rating, 263 reviews

EPIC Stowe Getaway - Great For Families & Friends

ColeRating, 5 stars1 week ago
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.
Guest favorite
Condo in Jeffersonville
4.91 out of 5 average rating, 154 reviews

In Resort 5* Smuggs Pass/Camp inc Mt View Nr lift!

TiffanyRating, 5 stars1 month ago
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.
Top guest favorite
Guesthouse in Westfield
4.99 out of 5 average rating, 141 reviews

Beautiful Chalet minutes to Jay Peak Resort

JackRating, 5 stars1 month ago
House is even better in person: high quality furnishings, beds, etc. Florence was very easy to communicate with and even helped us get some lift tickets. Highly recommend.

Private, pet-friendly home rentals

Top guest favorite
Guesthouse in Hinesburg
4.96 out of 5 average rating, 154 reviews

Cozy cottage in peaceful location

TrevorRating, 5 stars1 month ago
We had such a fun trip! Nikki’s cottage was absolutely gorgeous, nestled in the countryside. Would absolutely stay here again!
Guest favorite
Cabin in Starksboro
4.88 out of 5 average rating, 281 reviews

Charming getaway tucked away in the Green Mtns

SarahRating, 5 stars1 month ago
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.
Top guest favorite
Home in Chazy
5 out of 5 average rating, 14 reviews

Cozy 2 bedroom true log cabin

TimRating, 5 stars7 months ago
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.
Superhost
Chalet in Jay
4.9 out of 5 average rating, 142 reviews

Cedar Chalet in the Adk's -Dog friendly

JennyRating, 5 stars1 month ago
A Perfect Mountain Retreat! Our stay at Amy’s cabin was absolutely amazing. Nestled in the heart of AuSable Acres, the location offers a sense of serenity that’s hard to find elsewhere. The cabin itself is cozy and beautifully decorated, with everything you need for a comfortable stay. The fireplace was a highlight, especially on chilly evenings, and the kitchen was well-equipped for cooking meals with a view. I also appreciated the thoughtful touches, like the local guidebook and extra blankets. The host was incredibly welcoming and responsive, ensuring everything was perfect from check-in to check-out. I highly recommend this cabin to anyone looking for a peaceful escape in nature. It’s the perfect spot to unwind, recharge, and soak in the beauty of the area. I can’t wait to come back!
Guest favorite
Island in Hinesburg
4.96 out of 5 average rating, 165 reviews

1 Acre Private Island Cottage (Sat Check In/Out)

MonikaRating, 5 stars8 months ago
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!!
Guest favorite
Apartment in Montpelier
4.87 out of 5 average rating, 696 reviews

Entire 2nd Floor Walk to Montpelier

IanRating, 5 stars1 week ago
Felt right at home. A nice spacious place for us to stay on our way to Montreal.
Top guest favorite
Apartment in Lake Placid
4.91 out of 5 average rating, 353 reviews

Whiteface View Retreat STR # -200022

CaseyRating, 5 stars1 month ago
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.
Top guest favorite
Guest suite in Weybridge
4.98 out of 5 average rating, 332 reviews

Beautiful 1 Bedroom Suite with private entrance

KristenRating, 5 stars1 week ago
Christine's place was wonderful! very comfortable bed, warm , all that you need to feel at home. We highly recommend.

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