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

Lakefront holiday home with kitchen and patio

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

It doesn't get more Vermont than this
Winter Wonderland
Let it snow
6 foot snow man - lasted until spring
Snow means snuggling

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Barbecue grill
  • Parking available
  • Dryer
  • Washer
  • Fireplace

Explore the area

View map
Chester, VT
  • Place, Weston Playhouse
    ‪16 min drive‬
  • Place, Magic Mountain Ski Resort
    ‪18 min drive‬
  • Place, Okemo Mountain Resort
    ‪31 min drive‬
  • Airport, Springfield, VT (VSF-Hartness State)
    ‪25 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Small Bedroom

2 Single Beds

1 bathroom

Bathroom 1

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

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

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

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: limit 2 total
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is required for transport to and from this property

About the area

Chester

Located in Chester, this holiday home is in the city centre and on a lake. Weston Priory and Phineas Gage Memorial are local landmarks, and some of the area's attractions include DaVallia Art & Accents and Bonnie's Bundles Dolls. Vermont Country Store and Vermont Museum of Mining and Minerals are also worth visiting. Enjoy the area's slopes with cross-country skiing and snowboarding, and don't miss out on the snowmobiling and ice skating.
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Map
Chester, VT

What's nearby

  • Weston Playhouse - 16 min drive - 15.5 km
  • Magic Mountain Ski Resort - 18 min drive - 21.1 km
  • Weston Priory - 22 min drive - 22.9 km
  • Vermont Country Store - 22 min drive - 25.4 km
  • Okemo Mountain Resort - 31 min drive - 34.3 km

Getting around

  • Bellows Falls Station - 29 min drive
  • Springfield, VT (VSF-Hartness State) - 30 min drive

Restaurants

  • ‪Chester Country Girl Diner - ‬15 min drive
  • ‪Southern Pie Cafe - ‬13 min drive
  • ‪MacLaomainn's Scottish Pub - ‬13 min drive
  • ‪Subway - ‬14 min drive
  • ‪The Hub At Weston - ‬18 min drive

Frequently asked questions

Is Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required pet-friendly?

Yes, this property allows pets (limit 2 total).

What time is check-in at Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required?

Check-in begins at 4:00 PM.

What time is check-out at Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required?

Checkout is at 11:00 AM.

Where is Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required located?

Located in the heart of Chester, this holiday home is 5.9 mi (9.5 km) from DaVallia Art & Accents and within 12 miles (20 km) of Bonnie's Bundles Dolls and Lowell Lake State Park. Green Mountain National Forest and West River are also within 12 miles (20 km).

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 213 out of 227 reviews
Rating 8 - Good. 12 out of 227 reviews
Rating 6 - Okay. 0 out of 227 reviews
Rating 4 - Poor. 1 out of 227 reviews
Rating 2 - Terrible. 1 out of 227 reviews

Reviews

10/10 Excellent

Karon J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Sep 2025

10/10 Excellent

Deborah C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Aug 2025

10/10 Excellent

Ian G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 5 nights in Jul 2025

10/10 Excellent

Jessica G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Wedding

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.
Stayed 4 nights in May 2025

10/10 Excellent

Jenn R.

Liked: Cleanliness, check-in, location, listing accuracy

Amazing, Cozy Ski Cabin

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.
Stayed 3 nights in Jan 2025

10/10 Excellent

Josh B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ski Trip

Had a great overall trip! Pictures were accurate and was perfect as a home base for our ski trip.
Stayed 4 nights in Feb 2024

10/10 Excellent

Sarah G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Getaway!

Our family had such a wonderful time staying at this property. The house is quaint but has everything you need, and the property is breathtaking. We would stay here again in a heartbeat!
Stayed 3 nights in Mar 2023

10/10 Excellent

Laureen I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

This place is beautiful!

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!
Stayed 4 nights in Nov 2024

10/10 Excellent

Allen F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!

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!
Stayed 3 nights in Aug 2024

10/10 Excellent

Tania B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Very Comfortable Cabin

My partner, my chiweenie and I were very pleased with our stay at this comfortable, cozy cabin! If you're looking to get away, this is it. At the same time, restaurants and several ski areas are just a short drive away. Highly recommend and we hope to stay here again!
Stayed 6 nights in Feb 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful country escape

We had an amazing time just relaxing on the property and exploring some local towns & hikes. The cottage was so charming, we loved sitting by the indoor fire and outdoor chiminea. It was a most peaceful getaway and I must say I got the best night’s sleep while there.
Stayed 4 nights in May 2023

10/10 Excellent

Leila M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Secluded, cozy, clean cottage

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!
Stayed 4 nights in Aug 2024

10/10 Excellent

Jesse A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise in the mountains!

The property owners Dawn and Bob were so hospitable and friendly. We love the place and hope to be back again next summer! Thank you!!!
Stayed 7 nights in Jul 2022

10/10 Excellent

Jeremy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Annual midwinter excursion

This is our second year renting this place now, and we have fallen in love! We will be back year after year Honestly, my wife and I would consider purchasing the property if the opportunity ever arose
Stayed 3 nights in Feb 2023

10/10 Excellent

Svetlana K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute and super cozy cottage in Chester, VT

Thank you Dawn for your hospitality! The cottage is very charming! Very conveniently located near Okemo mountain (20 min). The kitchen is very well equipt and nice, cozy, and clean. The cottage is full of "Vermont Charm". 5 stars!
Stayed 3 nights in Dec 2022

10/10 Excellent

Lainey L., Boston, MA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful getaway

Myself, my husband, our 2 children (ages 2 and 4) and our 2 dogs had a great long weekend at the cottage. The view was spectacular and large yard were exactly what we were looking for. Our kids loved the house and the horses across the street. Chester is a cute downtown to fulfill any of your needs. We had a great time and will definitely be back! Thank you Dawn and Sam for a wonderful time.
Stayed 4 nights in Apr 2023

10/10 Excellent

Steven W., Mountville

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great ski weekend

The cottage was a great stay for our ski trip to Vermont. The cottage is very welcoming and had everything we needed. it was comfortable throughout and we enjoyed the wood fire stove each evening after skiing. Beds were comfortable, the bathroom was supplied with plenty of towels and some toiletries and the kitchen had a good supply of pots, pans, dishes and plenty of basics for cooking and making coffee. We were only 25 mins from Okemo and 50 mins from Mount Snow so great for our ski plans. Communication and information from the host was great and we will definitely look to stay here again on our future trips.
Stayed 4 nights in Feb 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Glamping in Vermont!

This is a quaint little rustic cabin. All the basic amenities are provided, including plenty of bedding, dishes and fire logs. Consider this glamping with perks! The property was very accommodating for our two dogs and the views were beautiful. I would suggest that the only real improvement that is needed is to have the septic tank serviced once the snow is gone as there was an odor in the bathroom that could be a little overwhelming. I thank the owners of the property for our first Vermont experience to have been so memorable.
Stayed 5 nights in Mar 2023

10/10 Excellent

Susan L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute,cozy,cottage

If you want a peaceful vacation,this is the place you want to rent.There is plenty of hiking in the area,and plenty of shopping,not far from the cottage. The foliage is beautiful this time of year in Vermont. The owners are so nice,and their dog,Bailey, will come and visit you on the deck.The horses are friendly,and my husband had fun feeding them peanuts.We liked the woodstove and the chiminea. They were easy to light,and there was plenty of wood,on the deck for them.Thankyou,Dawn and Bob for your hospitality!We definitely enjoyed our stay! Sue and Dave L.
Stayed 8 nights in Sep 2023

10/10 Excellent

Diane P., Stamford, CT

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for our ski getaway!

This cozy house was perfect for my family’s ski getaway around New Year’s. Our arrival - marked by the picturesque horse farm across the street, Christmas lights leading the way to the house, and the smell of cinnamon inside - put us in the holiday spirit even though it felt like spring with the unseasonably warm temperatures outside. The house was just 20ish minutes from Okemo and made for a great home base for skiing. The wood stove was easy to use with chopped wood and kindling provided, allowing us to dry our ski clothes and making the house really feel like a cozy getaway. The kitchen had everything we needed (we had breakfast and dinner at the house every day, and also made our lunches to bring to the mountain with us). It was a really fun trip despite not so great weather, with lots of family bonding time skiing, playing board games, and watching movies, and this house helped make for a great experience. The only drawbacks (just one bathroom, and on a dirt road that got a little muddy given the warm weather), were known to us ahead of time and well worth the trade offs given the location, price, and other benefits of the house.
Stayed 3 nights in Dec 2022

10/10 Excellent

Stacey H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was lovely. We cooked both breakfast and dinner in the kitchen. The woodstove does heat the house very well.
Stayed 4 nights in Oct 2025

8/10 Good

Dorothy b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lots of little details making the visit special. Beautiful setting in the hills. Cozy fireplace,
Stayed 4 nights in Oct 2025

10/10 Excellent

Klondie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Oct 2025

10/10 Excellent

Paul Hopper A.

Liked: Cleanliness, check-in, location, listing accuracy
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.
Stayed 3 nights in Aug 2025

8/10 Good

Kathleen C.

Liked: Cleanliness, check-in, location, listing accuracy
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.
Stayed 6 nights in Sep 2025

About the host

Hosted by Dawn and Robert "Sam" Brown

Host profile image
We are Robert "Sam" and Dawn Brown - Sam was born in Vermont and I moved here when I was 13. We met in 8th grade and fell in Love. In Vermont you learn to reconnect with your friends, neighbors and family. It will be the most uplifting downtime you will ever have. Our two horses are generally right across the street and are very friendly as are all the neighbors. Don't worry about the road in the winter they keep it very well plowed and sanded. the picture is of us at Phelps Barn in Grafton VT on Christmas Eve.

Why they chose this property

It is the setting. Nestled away but open to a wide spectacular view. Horses, mountains, open fields and woods with a brook down on the lower road.
You get the sun in the morning and nice shade during the afternoon while you are out on the deck grilling .

What makes this property unique

DIRECTIONS - heading North on 103 into Chester keep going straight as the road turns into Route 11 go about 5.5 miles on Rte 11 then turn right onto the Chester/Andover road go 3/4 mile and just before the road starts to bend turn right onto the Potash Brook Road which is a dirt road. You will come to 2 forks, on the first go right and the second go left. all the dirt roads are dead ends so you can't get too lost. It is about 1.5 miles on the dirt road. You will see the white horse fence and big ARROW
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