Find Hotels with Free Wifi in Chester, VT
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Our top choices for Chester hotels with free wifi
8.2 out of 10, Very Good, (402)
"Lovely stay"
Christine
$129 nightly
The price is $141
Dec 16 - Dec 17
Total with taxes and fees
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
Paul
$197 nightly
The price is $215
Dec 29 - Dec 30
Total with taxes and fees
10.0 out of 10, Exceptional, (1)
"This was a wonderful experience for us.
The Inn and room were spotless. Very comfortable bed. We will return.
The only issue was the tub/shore. Too much of a challenge for older folks. "
Thomas
$179 nightly
The price is $200
Dec 14 - Dec 15
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!
Room in Historic Inn! 20 Minutes to Okemo!Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
Peter C.
$171 nightly
The price is $192
Dec 14 - Dec 15
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
Whimsical Room & Private Bathroom in Historic InnChester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
Paul S.
$181 nightly
The price is $203
Dec 14 - Dec 15
Total with taxes and fees
Historic 150-year-old farmhouse, Jacuzzi included
Historic 150-year-old farmhouse, Jacuzzi includedChester Depot
9.8 out of 10, Exceptional, (10)
"This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!"
Amy S.
$419 nightly
The price is $469
Dec 14 - Dec 15
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!Chester Depot
9.0 out of 10, Wonderful, (2)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together.
The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
Jacque
$198 nightly
The price is $222
Jan 4 - Jan 5, 2026
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
Chester Farmhouse Ski Retreat near SlopesChester Depot
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
Lori N.
$356 nightly
The price is $399
Jan 7 - Jan 8, 2026
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Chester Hotel Reviews
Pointe at Castle Hill Resort
10/10 Excellent
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