Beginning of main content
182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!
182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!

Cheap Chester Hotels

The Karass Inn

The Karass Inn

225 Pleasant Street, Chester, VT
    3.0 out of 5.0
     
     

    Located in Chester Depot, this bed & breakfast is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Gallery North ...

    $112

    Hugging Bear Inn and Shoppe

    Hugging Bear Inn and Shoppe

    244 Main Street, Chester, VT
      2.5 out of 5.0
       
       

      Located in Chester Depot, this bed & breakfast is within 9 mi (15 km) of Grafton Historical Society, Vermont Museum of Mining and Minerals, and Hunter Gallery ...

      $119

      Chester Vacation Deal FAQ's

      Where to find Chester package deals?

      On CheapTickets, you can find package deals in Chester as low as !

      When is peak season in Chester?

      February, July, October are very popular times to visit Chester.

      When is the best time to visit Chester?

      If you're looking for cheap vacations to Chester, April is the best time to visit Chester.

      When is the worst time time to visit Chester?

      Prices for Chester vacations can peak during November.

      When is low season in Chester?

      We have found December, April, November to be the least-crowded time of the year to visit Chester.

      Where is Chester?

      Calling all noble cheapskates, cheapaholics and cheapsters. There's never been a more perfect time to take your thrifty selves on a vacation to Chester!

      379 miles north-east of Washington is Chester You'll also get to Chester if you travel 7 miles north-west of Rockingham.

      Visitors to this area of Central Vermont- Killington will be rubbing shoulders with roughly 3,000 people.

      Cheap Things to do in Chester

      If the thought of excessive entry fees and ticket prices makes you anxiously clutch at your wallet, fear not — we've got you covered! These free activities in or near Chester will help you make the most out of your time and your budget:

      • Keep your eyes peeled for the awesome things going on at the DaVallia Art & Accents. This establishment is renowned for hosting some of the best free arts and culture events in the area. Study their forthcoming program and see what catches your eye!
      • The sight of rain falling through the trees is one of nature's most precious displays. If the clouds are hanging low, why not get your hands on a cheap raincoat or umbrella and soak up the ambience at Dorsey Park?

      Cheap Chester Vacation Package Deals

      You won't have to waste hours scouring the web for the cheapest deals on flights, accommodations and experiences when you book with CheapTickets. We've done the hard work for you already! And we promise that cheap doesn't always mean nasty.

      To travel cheaply is to give up all sorts of options, right? Wrong! With 500 partner airlines and over 500,000 properties around the world, you're loaded with choice. And the best part is you'll save up to $330^ if you combine your bookings on hotels and flights.

      Your inner cheapskate can sleep easy with our Price Guarantee. It works like this — if within 48 hours you've found your package deal for a lower rate, we'll match it and give you back the difference. How's that for penny pinching!

      Get CheapCash

      What could be more awesome than nabbing the cheapest deal around? A cheap deal with extras! With our rewards program, you'll be able to save cash on your next CheapTickets hotel stay just by booking your flights.

      Could CheapCash be easier? Simply log in or sign up free of charge, join the program, and you'll have access to thrifty bonus offers and perks — and of course you'll save on all your eligible bookings. It's minimum effort for maximum rewards!

      Cheap Car Rentals in Chester

      So, cheapster — you don't have the patience for catching public transportation, but you're looking for a cheap way of getting about in Chester, right? Why not see all the sights from your own rental car? You'll find it's way more fun than being on a packed bus or train, and you'll get to control the music!

      Cheap Hotels in Chester

      Can't make up your mind where to get a room? A few leading options include the Rose Arbour Bed & Breakfast and the Hugging Bear Inn and Shoppe.

      ^Savings based on all package bookings made with Flight + Hotel on CheapTickets.com from January 1, 2018 to December 31, 2018, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. 

      *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.