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Cozy Historic Hilltop Cottage with Mount Ascutney View

Photo gallery for Cozy Historic Hilltop Cottage with Mount Ascutney View

A deck with a metal chair and a decorative vase, overlooking a forested area with autumn foliage.
A living room with a brick fireplace, wooden beams, a dining area with chairs, and a red armchair.
A wooden staircase leading to a second floor, a wooden chair, a small table with a lamp, and a radiator on the wall.
A cozy living room with a fireplace, a dining table set for four, and a comfortable sofa.
A two-story wooden house with a brick foundation, a front porch, and a small stone retaining wall.

Reviews

9.6 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Barbecue
    A rare find - perfect for a relaxed, outdoor grilling experience.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Internet
  • Onsite parking available

Explore the area

View map
West Windsor, VT
  • Place, Mt Ascutney State Park
    ‪5 min drive‬
  • Place, Fifth Avenue
    ‪6 min drive‬
  • Place, T-Bar
    ‪7 min drive‬
  • Airport, Springfield, VT (VSF-Hartness State)
    ‪28 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Double Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Garden
Dining area

Add dates for prices

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About the area

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 try out other outdoor activities such as snowmobiling and sledging.
View more Cottages in WindsorOpens in a new window
Map
West Windsor, VT

What's nearby

  • Mt Ascutney State Park - 5 min drive - 3.6 km
  • Ascutney Outdoors - 6 min drive - 2.9 km
  • Fifth Avenue - 6 min drive - 3.6 km
  • Broadway - 6 min drive - 3.6 km
  • T-Bar - 7 min drive - 4.0 km

Getting around

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

Restaurants

  • ‪Harpoon Brewery - ‬19 min drive
  • ‪Frazer's Place - ‬15 min drive
  • ‪The Hartland Diner - ‬21 min drive
  • ‪Windsor Pizza Chef - ‬14 min drive
  • ‪Skunk Hollow Tavern - ‬20 min drive

Frequently asked questions

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

No, pets are not allowed at this property.

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

As of 29 October 2026, prices found for a 1-night stay for 2 adults at Cozy Historic Hilltop Cottage with Mount Ascutney View on 31 October 2026 start from NZ$932, 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.

How much is parking at Cozy Historic Hilltop Cottage with Mount Ascutney View?

On-site 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?

Checkout is at 11:00 AM.

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

Situated in the mountains, this cottage is within 2 miles (3 km) of Ascutney Outdoors, Rope Slope and Rope Tow. T-Bar and Main Slope are also within 2 miles (3 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 73 out of 89 reviews
Rating 8 - Good. 12 out of 89 reviews
Rating 6 - Okay. 3 out of 89 reviews
Rating 4 - Poor. 1 out of 89 reviews
Rating 2 - Terrible. 0 out of 89 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 review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the third time we have stayed at the old schoolhouse. Location is great for going into Lebanon or Woodstock. The stairs seemed steeper to get to the bathroom from the bedrooms upstairs, but that’s just us showing our age. All in all it’s a good place to relax and enjoy lovely Vermont.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
If you love history, this is the place. Quaint, quiet, clean and cozy. Beautiful view from the back porch. Even has a record player with records (aka-albums, vinyls).
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

6/10 Okay

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

Graduation

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

4/10 Poor

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 review

8/10 Good

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
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