Main Street Chester Hotels

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We Price Match. So if you book and find a hotel on Main Street in Chester cheaper? We will refund the difference!

Looking for a hotel on Main Street in Chester?  Enter your travel dates to compare available hotels on Main Street Chester only or browse the list below to see all hotels found on Main Street Chester. If you do wish to see a wider view of Chester then please select 'All' Chester hotels when you select your dates.  Please also see the map showing just the hotels along Main Street Chester.

Hugging Bear Inn

244 Main Street Chester VT 05143

Located in Chester, Vermont, this Victorian bed and breakfast boasts an on-site Teddy bear gift shop and a full daily breakfast. Free Wi-Fi is available in every room. Every guestroom at the Hugging B...more

Superb 9.3/10
Score from 96 reviewers
2 star
266 Main Street Chester VT 05143

Located 10 miles from Magic Mountain Ski Area, this Chester, Vermont inn features a fireplace in all rooms. Free Wi-Fi is also provided in each room. Each room provides an en suite bathroom at The Che...more

Fabulous 8.9/10
Score from 73 reviewers
5 star
321 Main Street Chester 05143

This Victorian bed and breakfast in Chester, Vermont boasts a gourmet breakfast and uniquely styled guest rooms. Okemo Ski Mountain is 20 minutes’ drive away. Inn Victoria features rooms decorated in...more

Superb 9.6/10
Score from 68 reviewers



Last updated: 21 Oct 2019

Book now and pay later rooms are subject to availabilty.

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