Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required

Chester, Vermont
$155 avg/night
Bed 2

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 4

Max Sleeps

Adorable Cozy Cottage - sits on a mountainside with an OMG view- ideal for Cyclist, Skiers, Fall Leaf Peakers, Summer get away. 10 minutes from Historic Weston, 10-40 minutes from 4 major ski areas, Magic, Okemo, Bromley and Stratton. Sleigh rides and winter activities as well as many summer activities close by. Plenty of room for children to play. bedrooms are upstairs and the bathroom is on the main floor.

Weekly and Monthly rates available

  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • SKI

    Cross-country Skiing And Snowboarding Nearby
  • PETS

    2 Total Pets Pet Friendly Service Animals Exempt From Fees
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • KITCHEN

    Blender Coffee/tea Maker Microwave Oven Paper Towels Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Garden Outdoor Furniture Patio
  • BATHROOMS

    1 Bathroom Hair Dryer Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Hiking Nearby Kayaking Nearby Mountain Biking Nearby Power Boating Nearby Sledding Nearby Snowmobiling Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Stair Gate
  • LOCATION HIGHLIGHTS

    In The City Center In The Mountains Near A Hospital On The Lake
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Availability

Review Review

  • Sarah D.

    Submitted Mar 10, 2026

    Stayed Mar 5, 2026

    Adorable and perfect accommodations! Horses were a lovely surprise.

  • James R.

    Submitted Mar 1, 2026

    Stayed Feb 25, 2026

    Great stay, the cottage was equip with firewood and everything we needed to stay cozy! Always a great view !

  • Stephen B.

    Submitted Mar 1, 2026

    Stayed Feb 5, 2026

    Beautiful house. 20ish minutes to Okemo. Perfect ski house for a small group. Would absolutely recommend it and I plan on returning!

  • debbie c.

    Submitted Jan 30, 2026

    Stayed Jan 26, 2026

    Cabin was so nice, with really nice winter touches. Host & family very responsive when issue with TV & internet went out. My 3rd trip here..just as great in winter, as summer!!

  • Thatcher W.

    Submitted Jan 19, 2026

    Stayed Jan 16, 2026

    They were great thankYou

  • Teagen H.

    Submitted Jan 9, 2026

    Stayed Dec 26, 2025

    Very cozy and great view

  • Christine T.

    Submitted Jan 4, 2026

    Stayed Dec 29, 2025

    Our first ski trip to Vermont was made perfect with our stay at this warm and cozy cottage. From the moment we booked this cabin Dawn provided very detailed directions. It is remote but it was very easy to find. Our trip was in snowy, icy weather but the dirt roads were plowed as well as the driveway so accessibility was no problem. A fire was ready for us to light, Christmas tree was glowing and we felt so welcome. Every detail regarding our stay was well documented in a binder and if we had had a question or problem communicating with Dawn was easy. We had a power outage one night but we felt well equip with plenty of firewood, lanterns, candles and extra batteries. Kitchen was well stocked with all the essentials, beds were so comfy with down comforters and we loved all the seasonal decorations. There was nothing we needed to make our stay more comfortable or enjoyable. We loved staying at this cottage and can’t wait to get the chance to come back.

  • Ben E.

    Submitted Dec 26, 2025

    Stayed Dec 23, 2025

    We love Dawn’s place and have stayed here many times. Dawn is a wonderful host and the cabin is very comfortable.

  • eunice E.

    Submitted Dec 8, 2025

    Stayed Dec 5, 2025

    Absolutely a great place very well maintained and hopefully we will visit again soon!

  • Paul M.

    Submitted Dec 2, 2025

    Stayed Nov 25, 2025

    Cleanliness, quiet, accommodating.

  • Submitted Nov 24, 2025

    Stayed Nov 13, 2025

    I did not meet anyone during my stay. The amenities were as described. I enjoyed my and I love Vermont.

  • karen g.

    Submitted Nov 18, 2025

    Stayed Nov 8, 2025

    Another wonderful stay in this special place. Cottage is clean, cozy, and the setting is beautiful. I've been coming here for years, and it never disappoints!

  • Brandon S.

    Submitted Nov 6, 2025

    Stayed Nov 2, 2025

    Perfect, no complaints, wouldn't change anything

  • Stacey H.

    Submitted Oct 27, 2025

    Stayed Oct 23, 2025

    The cottage was lovely. We cooked both breakfast and dinner in the kitchen. The woodstove does heat the house very well.

  • Dorothy b.

    Submitted Oct 19, 2025

    Stayed Oct 15, 2025

    Lots of little details making the visit special. Beautiful setting in the hills. Cozy fireplace,

  • Klondie L.

    Submitted Oct 13, 2025

    Stayed Oct 10, 2025

    This cottage has all the amenities you could think of, we felt right at home immediately! The view is impossible to beat and we really enjoyed visiting the horses next door! The wood stove was perfect for chilly fall evenings! Would stay again in a heartbeat!

  • Karon J.

    Submitted Oct 3, 2025

    Stayed Sep 26, 2025

    Dawn was wonderful! She is a Gem! The place was clean and inviting. Very dog friendly. It is so quiet and peaceful! The view was absolutely AMAZING!!!! We so enjoyed our stay there.

  • Paul Hopper A.

    Submitted Sep 17, 2025

    Stayed Aug 17, 2025

    The cottage was just as depicted in the listing. We found it cozy and comfortable - and, yes, we found it without any trouble despite the directions that initially gave us pause. We especially loved spending mornings and evenings on the deck overlooking a meadow. The kitchen was equipped with everything we needed and we cooked every evening, dining by a fire in the chiminea that was just wonderful.

  • Kathleen C.

    Submitted Sep 15, 2025

    Stayed Sep 7, 2025

    A beautiful location with great green mountain views. House is quirky buut comfortable. Stairs are very steep. Needs some updating. Great wood stove with lots of firewood and kindling. Quiet location on a dirt road. Close to Chester, Weston and Londonderry. Nice restaurants nearby.

  • Deborah C.

    Submitted Aug 27, 2025

    Stayed Aug 8, 2025

    A little piece of Heaven on earth. Dawn is a great host. The horses added to the charm, along with daily visits from Bailey. Definitely will be back.

  • Frank C.

    Submitted Aug 21, 2025

    Stayed Aug 3, 2025

    The house was just as we remembered it. The mountain view from the deck was spectacular. We were so happy to see the horses in the yard! Our pups loved it too! We found an amazing butcher near by, best steaks we've ever had! We grilled each night and loved it. The maple creemees are a must try. Each night ended with a nice fire on the deck and a view that can't be matched. We'll be back!

  • Stacy D.

    Submitted Jul 30, 2025

    Stayed Jul 26, 2025

    Central to all we wanted to do. So relaxing!! Our favorite thing to do was to sit on the back deck. We worked, played games, crafted, are our meals, and sipped coffee enjoying the beauty of the area!! Thanks!!!

  • Ian G.

    Submitted Jul 28, 2025

    Stayed Jul 20, 2025

    It was by far the best vacation my family has had in forever the of the stars at Night from the porch were worth 1 million bucks the kindness and help of the caretakers and Dawn was first class. Excellent location best nights of sleep in my family and I have had in a long time felt like we were at home thank you thank you

  • Pam D.

    Submitted Jul 22, 2025

    Stayed Jul 16, 2025

    We had the best time. The view is certainly a “million dollar” view. We could not have had a better experience.

  • Gail M.

    Submitted Jul 6, 2025

    Stayed Jul 3, 2025

    You are lucky if you get the chance to stay here. The cottage has everything you need including nice bedding and toiletries. The property is a horse farm with rolling meadows, sunshine, fresh air and peace. I hope I get the chance to come back again.

  • Suzanne B.

    Submitted Jul 3, 2025

    Stayed Jun 11, 2025

    This was such a lovely place to stay! The cottage itself is very homey and well-equipped, with a gorgeous view of the surrounding mountains - very green in the summer time. My college-age kid and I stayed for three weeks to get some serious down-time, and this was the perfect place. The cottage was very comfortable, with Vermont-y decor and a complete kitchen. The deck is a great place to hang out and watch the horses grazing in the pasture by day, and fireflies by night. It's close to Chester, which is a sweet little village with a well-stocked market (Smitty's) that has a surprising amount of gluten-free food. The owners provide a lot of information on the surrounding area, as well, though we mainly stayed put and walked the local roads and in the forest. It was a perfect rural retreat. I hope we get to stay here again someday!

  • Gary V.

    Submitted Jun 10, 2025

    Stayed Jun 7, 2025

    The property was not well kept. Something had expired under the bathroom floor or wall. Sign said to keep window open, definite dead animal smell. Outside not as pictured or described. Very unkept, not rustic. Dead lawn mower in high yard. Bitten by spider, treadbare towels, same cleaning sponge used to clean bathroom after every stay...not sanitary. Same with kitchen sponge. We left after one night and incurred extra expense finding suitable lodging. Could be a nice place if better cared for. Definitely not Premier Host.

  • Allen F.

    Submitted Jun 4, 2025

    Stayed May 22, 2025

    What a lovely place and wonderful owners!Our second stay, hope to stay many more times.Very relaxing, lovely view. A blessing.

  • Jessica G.

    Submitted Jun 2, 2025

    Stayed May 29, 2025

    This is the perfect Vermont cottage you would picture in your mind. Myself and my two adult kids traveled from Virginia and fell in love with the place. The scenic views are amazing. The place is so quaint we kept the fireplace going laughed a lot and had a wonderful time. We absolutely will stay there again.

  • Romain G.

    Submitted Apr 2, 2025

    Stayed Mar 21, 2025

    Great stay, as advertised, would stay again

  • Erik M.

    Submitted Mar 10, 2025

    Stayed Feb 22, 2025

    Great cabin! We’ve stayed here before and we’re excited to come back. Love this cabin and owners were very responsive.

  • Stephanie C.

    Submitted Feb 23, 2025

    Stayed Feb 16, 2025

    I can't say enough about how wonderful this cabin is. Every part of it was well planned, from the furniture to the drinking glasses. It's cozy with all the modern amenities. The view is outstanding and the neighbors are friendly and a special treat for horse lovers. Check in was a breeze and the cabin was very clean. Can't recommend it enough!

  • Yura S.

    Submitted Feb 16, 2025

    Stayed Feb 13, 2025

    Wonderful house and even better hosts, my family and I enjoyed our stay there.

  • James R.

    Submitted Feb 3, 2025

    Stayed Jan 30, 2025

    We had a very pleasant stay at the cottage while on our quick ski trip to okemo. Cottage has the most beautiful morning views, probably the best I’ve ever had at a rental property in VT! Driveway and deck were shoveled and roads were plowed after any fresh snow, and cottage was very cozy.

  • Ben E.

    Submitted Jan 31, 2025

    Stayed Jan 24, 2025

    We have stayed here many times and love it. Very comfortable and relaxing with beautiful scenery. Dawn is an excellent host.

  • Robert G.

    Submitted Jan 18, 2025

    Stayed Jan 6, 2025

    This was a great little space, especially for my wife and I. We had planned to have several side trips, but it was so cold and the fire and the view kept us happily inside. We cooked several meals in the cabin and then enjoyed the view.

  • Jenn R.

    Submitted Jan 13, 2025

    Stayed Jan 10, 2025

    stayed here for a weekend while skiing at Okemo (25 min drive or so). Was perfect for our small group and had all the basics to cook at home as well. The horses across the street from the property made our day and were super friendly. We also loved the fire place. Would absolutely stay here again.

  • Winnie L.

    Submitted Jan 12, 2025

    Stayed Dec 25, 2024

    The cottage is clean and good size for our family. We enjoyed sitting in the dining room and looking out to the slope with beautiful view. We got to play sledding too. Bathroom is clean and kitchen has full cookware and utensils. Beds are comfortable, I am able to gain more sleep than on my own bed at home. We went to nearby mountains for skiing, also tried out some good local restaurants. The place has beautiful decoration, feels very cozy. The horses that are in the barn by the entrance are very friendly. We all had a great time, and would definitely come back.

  • Kristen F.

    Submitted Jan 10, 2025

    Stayed Dec 31, 2024

    This is our 4th year in a row renting this house for a winter vacation. Our family loves it and we'll be back again next year! The house is well equipped for a family, we've been bringing our son since he was 3. Dog friendly too! It is small, but very cozy and has everything you need to prepare meals and hang out, as well as laundry for longer stays or emergencies! Always very clean and well maintained.

  • Stephen

    Submitted Dec 15, 2024

    Stayed Dec 12, 2024

    House is great, exactly like the pictures. Plenty of wood! Sheets, blankets, towels, everything was great. Will book again if the timing works.

  • Laureen I.

    Submitted Nov 14, 2024

    Stayed Nov 10, 2024

    Our first night we just stayed in, we woke up to horses outside and it was so beautiful with the view! I would definitely recommend this cottage to family and friends! It is a family friendly place! The town was adorable! Overall, for my honeymoon, I was very happy with my stay and the trip!

  • Janice T.

    Submitted Nov 9, 2024

    Stayed Oct 23, 2024

    Great stay from start to finish. This vacation was just what the doctor ordered. A much needed destressor, no political nonsense. Bailey, the dog was a pure joy, as were thehorses.

  • David P.

    Submitted Oct 22, 2024

    Stayed Oct 17, 2024

    We had a great stay, what an amazing location and view. The hosts we very helpful and friendly, we loved seeing the horses, and wild turkeys and a few deer! Wish we lived there!

  • Wayne S.

    Submitted Oct 14, 2024

    Stayed Sep 30, 2024

    We spent ten days at this Vermont cottage. The host always responded quickly. The cottage was clean and had everything we needed. The views from the deck were perfect for viewing the beautiful Vermont fall foliage. We highly recommend this cottage for anyone looking to spend time in Vermont.

  • Eileen B.

    Submitted Sep 29, 2024

    Stayed Sep 26, 2024

    Loved the horses and the big friendly dog. Very quiet area up some dirt roads with beautiful view of the changing leaves on the mountain

  • Susan L.

    Submitted Sep 26, 2024

    Stayed Sep 18, 2024

    This was our 4th time staying here at the cottage.It still is quiet and relaxing,except for the calls of barred owls in the woods,which we loved to hear.We always enjoy the chiminea on the deck and the cozy woodstove in the living room.The Vermont country store in Weston is a nice place to shop,and we had great weather for our stay here.Thankyou,Dawn and Bob for the bottle of maple syrup,and we still enjoy seeing your dog,Bailey and the beautiful horses.

  • wade s.

    Submitted Sep 21, 2024

    Stayed Sep 12, 2024

    Cozy, convenient, beautiful view. I watched the sun rise every morning

  • Allen F.

    Submitted Sep 7, 2024

    Stayed Aug 18, 2024

    What a great time we had, including our 14 year old son. Dawn and Bob were so kind and hospitable. House was very comfortable and clean. Great view, beautiful countryside, just what we needed. Hope to go back soon!

  • Elysian A.

    Submitted Aug 29, 2024

    Stayed Aug 23, 2024

    A friend and I stayed here for a few nights with our dogs, looking to decompress and get some fresh air. This little place is absolutely lovely, entirely what we needed. The view is breathtaking, the area so quiet and peaceful, and the owners were so friendly. There was something so serene watching the horses be walked out to graze in the grass behind the house every morning, and it was a treat to be able to feed them peanuts! The fire pit in the back was great, and the provided firewood amazing, too. Multiple times, our dogs had the joy of romping around the yard with the owners’ super friendly pup, Bailey, who was honestly a highlight for us! The road the house is on offers a nice hike, and there are trails and stuff nearby too; the owner was super knowledgable and had great suggestions for food, as well. We were sad to go, but we’re already looking forward to planning another trip.

  • Leila M.

    Submitted Aug 16, 2024

    Stayed Aug 12, 2024

    A very clean, very cozy little cottage that suited our goal of a relaxing retreat! Beautiful views from the deck. Owners Dawn and Sam are next door, who have a horse stable and Bailey their very friendly dog! We hope to return again!

  • Tammy B.

    Submitted Aug 9, 2024

    Stayed Aug 5, 2024

    This cabin was perfect for myself and spouse. It was quiet and secluded and overall a great place to stay. Thank you !

  • Geraldine M.

    Submitted Aug 5, 2024

    Stayed Jul 28, 2024

    We were looking for the kind of quiet relaxing atmosphere we found here. The hosts were great and respectful of our privacy. It's an older property but clean and comfy

  • Reed & Tricia P.

    Submitted Jul 22, 2024

    Stayed Jul 19, 2024

    As the first time great time at this little get away. Easy check in, great view and local hiking was amazing

Your dates are Available!

Total

Includes taxes and fees
$186+
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