Search Cheap Flights toChester
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Chester Flights as Low as $360
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 10 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$360 Roundtrip, found 1 day ago
$360
Roundtrip
found 1 day ago

Tue, Sep 9 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$363 Roundtrip, found 9 hours ago
$363
Roundtrip
found 9 hours ago

Wed, Sep 10 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$365 Roundtrip, just found
$365
Roundtrip
just found

Tue, Sep 9 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$367 Roundtrip, found 9 hours ago
$367
Roundtrip
found 9 hours ago

Mon, Sep 8 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$373 Roundtrip, found 1 day ago
$373
Roundtrip
found 1 day ago

Wed, Sep 10 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$375 Roundtrip, just found
$375
Roundtrip
just found

Mon, Sep 8 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$377 Roundtrip, found 9 hours ago
$377
Roundtrip
found 9 hours ago

Sun, Sep 14 - Wed, Sep 17
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$378 Roundtrip, found 6 days ago
$378
Roundtrip
found 6 days ago

Tue, Sep 16 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$379 Roundtrip, found 10 hours ago
$379
Roundtrip
found 10 hours ago

Wed, Sep 10 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$381 Roundtrip, just found
$381
Roundtrip
just found

Tue, Sep 9 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$383 Roundtrip, found 1 day ago
$383
Roundtrip
found 1 day ago

Tue, Sep 16 - Wed, Sep 17
TPA
Tampa Intl.
LEB
Lebanon Municipal
$385 Roundtrip, just found
$385
Roundtrip
just found

Tue, Sep 9 - Wed, Sep 17
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$387 Roundtrip, found 16 hours ago
$387
Roundtrip
found 16 hours ago

Mon, Sep 8 - Thu, Sep 18
TPA
Tampa Intl.
LEB
Lebanon Municipal
$387 Roundtrip, found 9 hours ago
$387
Roundtrip
found 9 hours ago

Sat, Sep 13 - Sat, Sep 20
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$388 Roundtrip, found 6 days ago
$388
Roundtrip
found 6 days ago

Wed, Sep 10 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$390 Roundtrip, just found
$390
Roundtrip
just found
Last Minute Hotel Deals in Chester

Fullerton Inn
40 The Common, Chester, VT
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (368 reviews)
"No TV. No Elevator. Breakfast was lacking. Staff was wonderful and friendly. Rooms clean. Bathrooms are very tight but to be expected with the age of the inn. Loved the balcony off the room. We sat outside and played cards. Quiet area and restaurant downstairs."
Reviewed on Jul 14, 2025

Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (525 reviews)
"Service and concierge were excellent. Property was kept in a beautiful condition. Lost of inspiring rooms."
Reviewed on Jul 13, 2025

Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.6/10 (1,000 reviews)
Very good last-minute stay
"I booked this room last-minute but checkin was smooth, room was comfortable. I like that there are two restaurants in walking distance."
Reviewed on Jul 14, 2025

Kimpton Taconic Hotel by IHG
3835 Main St., Manchester, VT
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
9.2/10 Wonderful! (779 reviews)
"I love that the hotel is dog friendly and have bikes and scooters available for guests. The room was comfortable and clean, nicely furnished. Staff was outstanding"
Reviewed on Jul 15, 2025

The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
7.2/10 Good! (494 reviews)
"The property was historic and very quaint and the common areas were nice. Coffee was good. For the price paid -carpet in halls & elevator needed replaced/woodwork repainted. Air conditioner was a window unit/room outdated."
Reviewed on Jul 14, 2025

The Shire Woodstock
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (779 reviews)
"This is a lovely property in the town of Woodstock. We enjoyed our time there (and all the space in our room!). I left something in our room and did not realize it until the next day. I called the property to ask if anything had been found. They soon got back to me that they had my item and would ..."
Reviewed on Jul 10, 2025

Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8/10 Very Good! (845 reviews)
"Perfect accommodations for what we needed."
Reviewed on Jul 14, 2025

Latchis Hotel
50 Main Street, Brattleboro, VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (756 reviews)
"Amazing building with very knowledgeable and keen staff. Bustling city Centre but delivers comfort & an experience."
Reviewed on Jul 4, 2025
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.
Popular Flight Routes
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Top Chester Hotels
- Woodstock Inn & Resort
- Colonial Motel And Spa
- Kimpton Taconic Hotel by IHG
- The Equinox Golf Resort & Spa
- Hampton Inn Brattleboro
- Latchis Hotel
- Comfort Inn & Suites Brattleboro I-91
- Best Western Plus Keene Hotel
- Hampton Inn and Suites Manchester
- The Covered Bridge Inn
- Keene Elm City Hotel, Ascend Hotel Collection