Chester Holidays from £1,032
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Your Chester Holiday
Excellent adventures await when you reserve a Chester holiday package. Whether you're a history buff, art enthusiast or just a traveller who loves to experience new places, there's something for everyone in this lively city. Need some ideas on what to see or do first during your trip to Chester? Don't miss leading attractions like DaVallia Art & Accents. Your ultimate Chester holiday is just clicks away. Search flights, accommodation and more on Expedia for a trip that's tailored to suit your travel style.
Top Chester Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
Price was £1,209, price is now £1,032 per person
£1,032
per person
7 May - 14 May
found 5 hours ago
Return direct flight included
London (LHR) to Springfield (VSF)
8.6/10 Excellent! (853 reviews)
The hotel is charming. The location is great. The building is funky, given it's age and need for repair. The staff are friendly, helpful, and knowledgeable. The theater located in the same building is a one of a kind attraction. It was a plus for us that the hotel is owned and run by a nonprofit.
Reviewed on 22 Mar 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was £1,367, price is now £1,263 per person
£1,263
per person
7 May - 14 May
found 5 hours ago
Return direct flight included
London (LHR) to Springfield (VSF)
8.8/10 Excellent! (1,002 reviews)
Staff was very courteous. The hot soup in the lobby was a nice touch! Loved the breakfast selections.
Reviewed on 1 Mar 2026
The One Cat B&B
Price was £1,460, price is now £1,380 per person
£1,380
per person
7 May - 14 May
found 5 hours ago
Return direct flight included
London (LHR) to Springfield (VSF)
9.6/10 Exceptional! (79 reviews)
We loved everything about our stay. Our hosts were very kind, and put generous effort into providing delicious breakfasts, giving suggestions about local attractions, and allowing us as much or as little cat time as we wanted. The room we were in was very cozy, with a comfortable bed, and thoughtful touches such as a water kettle for tea or coffee, a small fridge, and a TV setup we didn’t take advantage of. The private bathroom down the hall was clean and had everything we needed. I would recommend this lovely B&B to anyone who likes cats and doesn’t have mobility issues that would prevent them from getting up stairs. Thank you to Pat and Conrad for a wonderful stay!
Reviewed on 17 Oct 2025
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Lebanon Municipal Airport (LEB) |
Population | 3,000 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Okemo Mountain Resort, Weston Playhouse and Weston Priory |
Top hotels in Chester
Fullerton Inn
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
The price is £106 per night from 3 Apr to 4 Apr
£106
3 Apr - 4 Apr
includes taxes & fees
8/10 Very Good! (424 reviews)
Yes, little guests easy parking spaces. Restaurant staff were pleasant. Heat didn’t appear until 11PM. A tad chilly. Room was clean.
Reviewed on 20 Mar 2026
Stone Hearth Inn and Eatery
698 VT-11 Chester VT
Fully refundableReserve now, pay when you stay
The price is £155 per night from 30 Mar to 31 Mar
£155
30 Mar - 31 Mar
includes taxes & fees
9.2/10 Wonderful! (116 reviews)
Beautiful place. Rustic and restored beautifully to keep the charm. Talked with the owner over breakfast. Family business with an amazing restaurant. We will stay there again!
Reviewed on 25 Mar 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is £113 per night from 20 Apr to 21 Apr
£113
20 Apr - 21 Apr
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
There's a cute little town nearby with a great coffee shop.
Reviewed on 26 Mar 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.