Chester, VT Villas Rentals

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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A large hotel with multiple buildings, a central courtyard, and a small pond.

1. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

Brownsville

$280 nightly

Nov 1 - Nov 2

Total with taxes and fees

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Top Chester Hotel Reviews

The Manchester View

10/10 Excellent

"We arrived at the Manchester View in late September on a trip to see the beautiful change of colors. View is definitely what you get here. Surrounded by gorgeous rolling hills and mountains that were covered with green, yellow, red and orange leaves. We were celebrating our 40th anniversary and were upgraded to a suite room. Thank you! Room was very nice, clean and spacious. My only complaint was the door would stick when trying to open or close the door to the room. And, although the bath was updated and very nice, the finish work around the counter wasn't complete. There was a gap between the wall and counter the ends didn't match up to the wall. But that is just really a minor issue. They also have a continental breakfast with the basics and a nice kick off to start your day. The view, the staff and did I say the view?... We would definitely stay here again!"

The Shire Woodstock

10/10 Excellent

"We had Deluxe King River view - deluxe has a fireplace and shares a balcony with rocking chairs. The room was great except a couple little maintenance issues (I told the front desk and hope they fix). And it’s a great location walkable to downtown, great views of river and hills, and the inn has fire pits ready to go. Too bad coffee makers are in the hallway, not in the room, and there’s no breakfast (they said they might start next year). We went nearby for breakfast, and a good market is just across the street."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"

The Jackson

10/10 Excellent

"This property is beautiful, peaceful, friendly, welcoming and far enough away from the green for a noiseless stay. The wine, cheese and bites that start your evening are lovely and gives you the opportunity to meet other guests if you choose. Ms. Walton, the host, was friendly, helpful and warm. She made me feel right at home. A magnificent place to stay in Woodstock Vermont"

On The River Inn

8/10 Good

"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."

Find out more about Chester

Chester Villas information

Number of reviews
Accommodation	27 Villas
Lowest Price	$305
Highest Price	$305

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If you want to make the most of your time in Chester, don't miss DaVallia Art & Accents. It's a favorite with locals and travelers alike.

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Our top choices for Chester villas

1. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

Find vacation rentals that suit your style

Top Chester Hotel Reviews

The Manchester View

The Shire Woodstock

Pointe at Castle Hill Resort

Jackson Gore Village, A Vail Resorts Property

The Jackson

Colonial Motel

On The River Inn

Aspen At Manchester

The Equinox Golf Resort And Spa

Find out more about Chester

Chester Villas information

Frequently asked questions

Explore a world of travel with Expedia

Villas in Chester

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chester villas

1. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

Find vacation rentals that suit your style

Top Chester Hotel Reviews

The Manchester View

Find out more about Chester

Chester Villas information

Frequently asked questions

Explore a world of travel with Expedia