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Cozy Historic Hilltop Cottage with Mount Ascutney View

Photo gallery for Cozy Historic Hilltop Cottage with Mount Ascutney View

Cottage on the hill
Cottage front
Deck with chiminea
Fall color from deck
Living/Dining room with gas stove

Reviews

9.6 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Swimming pool
  • Onsite parking available
  • Kitchen
  • Barbecue grill
  • Deck or patio
  • Free WiFi

Explore the area

View in a map
West Windsor, VT
  • Place, Mt Ascutney State Park
    ‪5 min drive‬
  • Place, Brownsville Trail
    ‪11 min drive‬
  • Place, Cornish-Windsor Covered Bridge
    ‪14 min drive‬
  • Airport, Springfield, VT (VSF-Hartness State)
    ‪28 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

1 bathroom

Bathroom 1

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Cozy Historic Hilltop Cottage with Mount Ascutney View

This exceedingly charming cottage on a wooded hilltop just outside of Brownsville has great views of Mt Ascutney and a burbling brook at the base of the hill. The historic converted early 1800's one room school house is filled with many antique furnishings. Hanging in the stairway are photographs of the house when it was the Hammond Hill School, with its teacher and her students. Enjoy the coziness of a gas fireplace in the living room or a wood fire in the chiminea on the deck. The cottage features a fully equipped and outfitted kitchen. Both bedrooms are upstairs, the master with a queen size bed and the second bedroom with a full-size double bed. The stairs are steep and may be a challenge for some individuals. All bed and bath linens are supplied.

Mt. Ascutney, only 5 minutes away, with opportunities for hiking, mountain biking or cross country skiing. There is easy access to the VAST trail network for snowmobiling, cross country skiing or snow shoeing. Mountain bikers will find some of the best single track trails in New England. Miles of great trails are accessible right from the house.
Ascutney Mountain Resort has many amenities including a shop for kayak and bicycle rentals. There is a full restaurant and bar available in the main lodge. In addition, the resort has outdoor tennis courts and a heated indoor swimming pool with an adjacent fitness room. There are several ski mountains in the area including Okemo, Killington, Suicide 6, Pico and Sunapee. There is no down hill skiing available at Ascutney. For you golfers, there are 5 courses only 15 to 45 minutes away.

The village of Woodstock, about 25 minutes from Brownsville is known world-wide for its artisans, its artists, and the galleries that show their works. It is also home to the Billings Farm, the Woodstock Inn and the Rockefeller Woodstock Resort. Nearby is the Green Mountain Horse Association in South Woodstock.

Close to Woodstock is the Village of Quechee where you’ll find the famous glass works factory of Simon Pearce with its retail shop of glassware and wonderful restaurant.

Nearby on the Connecticut river is the Cornish Art Colony with the home of Augustus Saint-Gaudens and the Maxfield Parrish museum.

There really is something for everyone any time of year!


Keywords: Ascutney, foliage, skiing, hiking, mountain biking, snowshoeing, cross country skiing, trails, horses, trails, Woodstock, Quechee, Okemo, Hanover, GMHA, antiques, golf
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
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

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 398760
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
Onsite 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 not indicated whether there is a smoke detector on the property

About the neighborhood

Windsor

Located in Windsor, this cottage is in the mountains. Cornish-Windsor Covered Bridge and Blow-Me-Down Bridge are local landmarks, and the area's natural beauty can be seen at Mt Ascutney State Park and Cornish Wildlife Management Area. Path of Life Garden and Maze of Adventure are also worth visiting. Take in the nearby slopes with cross-country skiing and snowboarding, or check out other outdoor activities such as snowmobiling and sledding.
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Map
West Windsor, VT

What's nearby

  • Mt Ascutney State Park - 5 min drive - 3.6 km
  • Brownsville Trail - 11 min drive - 10.8 km
  • Mount Ascutney Hospital - 12 min drive - 13.7 km
  • Cornish-Windsor Covered Bridge - 14 min drive - 14.4 km
  • Blow-Me-Down Bridge - 14 min drive - 14.7 km

Getting around

  • Windsor Station - 14 min drive
  • Springfield, VT (VSF-Hartness State) - 27 min drive

Restaurants

  • ‪Harpoon Brewery - ‬19 min drive
  • ‪Windsor Station Pub - ‬14 min drive
  • ‪Frazer's Place - ‬15 min drive
  • ‪Windsor Pizza Chef - ‬14 min drive
  • ‪The Hartland Diner - ‬21 min drive

Frequently asked questions

Does Cozy Historic Hilltop Cottage with Mount Ascutney View have a pool?

Yes, this property has a pool.

How much does it cost to stay at Cozy Historic Hilltop Cottage with Mount Ascutney View?

As of May 10, 2026, prices found for a 1-night stay for 2 adults at Cozy Historic Hilltop Cottage with Mount Ascutney View on May 11, 2026 start from $261, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Cozy Historic Hilltop Cottage with Mount Ascutney View pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Cozy Historic Hilltop Cottage with Mount Ascutney View?

Check-in begins at 4:00 PM.

What time is check-out at Cozy Historic Hilltop Cottage with Mount Ascutney View?

Check-out is at 11:00 AM.

Where is Cozy Historic Hilltop Cottage with Mount Ascutney View located?

Situated in the mountains, this cottage is 1.9 mi (3 km) from Mt Ascutney State Park and within 6 mi (10 km) of Paradise Park and Mt Ascutney Hospital and Health Center: Primary Care - Windsor. Mount Ascutney Hospital and Brownsville Trail are also within 6 mi (10 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 70 out of 84 reviews
Rating 8 - Good. 10 out of 84 reviews
Rating 6 - Okay. 3 out of 84 reviews
Rating 4 - Poor. 1 out of 84 reviews
Rating 2 - Terrible. 0 out of 84 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Paul H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful country! Very laid back atmosphere!Easy to check in and out. Great experience!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Ashley B.

Liked: Cleanliness, communication, location, listing accuracy
Disliked: Check-in
Nice quiet place to stay. We spent most of our time out and about but did cook one night on the grill outside , steaks from the local butcher in Brownsville that were incredible. The cottage is clean and as described. Definitely older, but has a lot of charm.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Emma C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy little cabin. Sweet time! We loved it.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Amy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful old schoolhouse with lots of charm! We loved having breakfast on the deck and a fire in the chiminea in the evenings. The house had everything we needed for our 5 night stay. Great location near historic sites, parks, the Connecticut River, and quaint towns.
Stayed 5 nights in Jul 2025
Verified

10/10 Excellent

Kevin C.

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

Great location for our vacation

Great location for our vacation. Owner was bery quick to respond to questionsz
Stayed 4 nights in Jul 2021
Verified

10/10 Excellent

Trisha S.

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

Great Stay in West Windsor

This place was just perfect for us! I highly suggest it for a place to unwind and just enjoy Vermont. Would stay here again for sure!
Stayed 3 nights in Jul 2021
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely weekend stay at this cottage! We greatly enjoyed our time here when we weren't out doing things (and the location was perfect for the activities we were doing). The back deck was a lovely place to sit in the fall weather, and we made good use of the kitchen and dining table for our meals.The bedrooms were comfortable. We liked the original wood in the house and the artwork on the walls. We hope to come back sometime!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Daniel G.

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

Perfect spot

Had a great stay at the old school house. Location was perfect for what we needed. Place was super clean and well appointed. Would love to come back again.
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Bill G.

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

Great getaway

Very quaint and quiet, great spot to visit all that you want in the area, or just to hang out and do nothing but enjoy the peace and quiet
Stayed 4 nights in Sep 2019
Verified

8/10 Good

Heather G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet, peaceful, cozy historic house with 2 bedrooms up steep stairs, and 1bathroom on main floor. Nice view from porch with some of Mt Ascutney visible. Well supplied kitchen. Second time here and would stay again. We wished the bed in larger bedroom was a bit more stable so it would not bounce whenever we moved a bit.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Adrien J.

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

Fantastic hilltop house

Fantastic hilltop house in the woods of Vermont; spotlessly clean, very comfortable and tastefully decorated, we had a wonderful stay.
Stayed 2 nights in Dec 2023
Verified

10/10 Excellent

Barbara R.

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

Truely charming, historical house

The house is nicely arranged and furnished. Everything necessary was supplied. Lovely deck with high quality gas grill. Well located for touring VT sites.
Stayed 3 nights in Jul 2023
Verified

6/10 Okay

Jamie O.

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

Graduation

Everything was perfect for our stay!!! Thanks!
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Andrew G.

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

Cozy house in Vermont

This house is exactly as described. It is in a very attractive location with good views and is very private. The house is much larger inside than it appears from the photos but still very cozy and is well equipped. It was spotlessly clean.
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

David T.

Cozy and Comfortable....

Enjoyed our 4 night stay. Accomodations comfortable for 4 adults and the location was ideal for our planned activities. The only feedback I'd add is it would be nice if there were an additional upholstered/recliner type chair in the family room for evening movies. Would highly recommend.this.great, historical home!
Stayed 4 nights in Aug 2018
Verified

10/10 Excellent

Gloria C.

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

Peaceful

We all enjoyed our stay here. After being in Niagara Falls for a few days it was nice to come here and relax before heading back to Maine. We enjoyed the peaceful atmosphere. The cottage is so quaint and the amenities were wonderful. We all had a wonderful time! We hope to return someday….
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

Jessica M.

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

Perfect Small Town Getaway

This was the perfect cottage for a winter getaway. I was solo, but the home could have easily accommodated many more. I loved the vintage touches and had a nice time listening to the classic vinyl records while enjoying a glass of wine and watching it snow. I had dinner outside on the patio one night and the view was lovely. It is just a few minutes drive from Woodstock and Quechee and I visited both several times. The cottage was clean and had everything I needed. Highly recommend for a quiet, relaxing stay.
Stayed 5 nights in Dec 2024
Verified

10/10 Excellent

Melanie D.

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

Connecticutt river trip 3 night trip

We wanted to be close to Great River Outfitters and we were. We also enjoyed White River Junction, Woodstock, alpacas, Sugarbush Farm and lots of good food and beer.We encountered a large spider web inside the back door and found the huge spider owner on the fireplace. I don't mind them so mush but My daughter had to dust for other crawlies.We could have used air conditioning the first night as it was so humid but other nights were quite pleasant.
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

David T.

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

Love VT!

This was our second visit to the VT schoolhouse since 2018. The same quaint charm and we love the location and atmosphere! Even in summer, the room fans kept us cool. Unfortunately due to Hurricane Henri, we were forced to return home after 2 nights out of 4 booked as the storm was forecast to hit directly at our home. Would highly recommend!
Stayed 4 nights in Aug 2021
Verified

10/10 Excellent

Elizabeth T.

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

Perfect Getaway

This property was the perfect accommodation for me and my husband as we road tripped across New England during the fall. The house was just as described. It sits on a bit of a hill. We enjoyed sitting on the deck with the small fire pit and drinking coffee. The house was cozy and close to town without being in town. I enjoyed the few historic pictures on the wall. I would recommend and if we are in this area again, I hope this property is available.
Stayed 2 nights in Oct 2022
Verified

10/10 Excellent

Verified traveler

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

Storybook Vermont Memories

My sister and I took my mom to Vermont for her 70th birthday. I chose this cottage because it was adorable and had a history. It was the perfect place for us to home base for a few days of general stores, covered bridges, Sugarbush Maple Syrup Farm, Dartmouth, King Arthur Four Company flagship store, and more. It was quiet and cozy. It does have a "very old house" smell to it - but it's a very old house. With 40F degree nights, the heater set to 65F worked great. Although we didn't have the chance to build a fire on the back patio, the supplies were available - as was everything else we needed! Thanks for a wonderful and memorable stay!!
Stayed 2 nights in Sep 2022
Verified

4/10 Poor

Dan B.

Liked: Cleanliness, check-in, communication
Disliked: Location

Disappointing Stay

Nice location and quaint little home. We had two issues with our stay. The neighbors were so loud celebrating the 4th of July that we had to leave in the afternoon to find a place to rest and relax before watching fire works in Hartland in the evening. The other issue was that the well water had an extremely strong sulfur smell to it and had the scent of rotten eggs. We were expecting something much quieter and wanted to spend time on the deck overlooking Mt. Ascutney but could not enjoy it due to the loud partying going on next door. Would not recommend this place to anyone looking for a peaceful relaxing place to stay. The description fell short of what was being advertised primarily due to loud neighbors.
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Kim R.

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

A Lovely Cottage

We enjoyed our stay here which was quiet and peaceful and full of charm. The 1 person kitchen is SUPER clean and well supplied with everything we needed. Bedrooms upstairs (bath is down) and watch you head going up the stairs you're over 5'4". Only took me once to learn. We played more records from their collection, rather than watching TV. Bed and linens very comfortable. I wish there had been more information/house rules provided for guests as we had no wifi access until direct contact with the owner who is off site but was very helpful once we reached through VRBO support. We were also interested in the history of the former schoolhouse which we didn't see anywhere. All that aside, we loved it and would go back!
Stayed 2 nights in Oct 2021
Verified

8/10 Good

Lisa T.

Liked: Check-in, location, listing accuracy

No Wifi and dusty

There was a thick covering of dust on all the surfaces on the first floor, which we cleaned off the next morning. Despite the ad indicating that Wifi/internet was available, it was not. We contacted the neighbor, Matt, per the Host's instructions, regarding the issue and also reached out to the host two times. Neither responded nor did the issue get resolved which was very disappointing as my son had work for his job to do and was unable to do so and nor were we able to use any cell phone. The stay just added additional stress to an already emotional trip (death in the family).
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Craig V.

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

A cozy comfortable quiet private cottage

We enjoyed our stay in the cottage. It was in a great private location that was quiet and peaceful. It had everything we needed. If it were a little warmer, we would've spent more time on the deck with the campfire and do some grilling, but we enjoyed lounging by the fire inside just fine. The price was reasonable. We would stay there again.
Stayed 2 nights in Oct 2022

About the host

Hosted by John

Host profile image

Why they chose this property

Our parents bought the cottage in 1977 as a vacation home. They always enjoyed staying there in all seasons. We have kept the cottage in the family as it always brings back wonderful memories.

What makes this property unique

The cottage is the perfect setting and location to enjoy all that New England has to offer in any season or to just sit by the fire or on the deck and read a good book.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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