Cheap Hotels in Chester, MA from $74

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Our top choices for Chester cheap hotels

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (844 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
$67 nightly
The price is $74
Apr 27 - Apr 28
Total with taxes and fees
Monument Mountain Motel

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
$102 nightly
The price is $114
Apr 29 - Apr 30
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (916 reviews)
"Such a cool and affordable place to stay in the Berkshires. Great lobby/bar with a good restaurant."
United States
Kathy
$92 nightly
The price is $103
May 4 - May 5
Total with taxes and fees
Berkshires Untold

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$71 nightly
The price is $78
Apr 28 - Apr 29
Total with taxes and fees
Pleasant Valley Motel West Stockbridge

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (137 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
$105 nightly
The price is $117
May 4 - May 5
Total with taxes and fees
River Valley Inn

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
8.0 out of 10, Very Good, (170 reviews)
"Very nice people in atmosphere all around"
United States
Michael
$108 nightly
The price is $124
May 5 - May 6
Total with taxes and fees
Baldwin Inn & Suites, SureStay Collection by Best Western

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
2.5 star property
Holyoke
$187 nightly
The price is $209
May 21 - May 22
Total with taxes and fees
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (851 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
$79 nightly
The price is $88
Apr 27 - Apr 28
Total with taxes and fees
Howard Johnson by Wyndham Lenox

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.2 out of 10, Wonderful, (433 reviews)
"Breakfast was exceptional. We couldn’t have been happier during our stay."
United States
Robert
$112 nightly
The price is $127
Apr 27 - Apr 28
Total with taxes and fees
Naomi's Inn Bed & Breakfast

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (576 reviews)
"Clean"
United States
Brian
$75 nightly
The price is $84
Apr 27 - Apr 28
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
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.

Find out more about Chester

How can I get cheap hotels in Chester?

Best tips to find a cheap hotel in Chester

  1. If you're looking to travel to Chester on a budget, you'll be happy to know that you can find hotels for as low as $74. Of course, that price is affected by amenities, star rating, and even the time of year you visit. At most, hotel prices can be as high as $209. Staying a short amount of time in Chester is an effective way to reduce hotel costs.

  2. When you cut your vacation down to just a few days, you don't have to worry as much about hotel prices since you don't have that many nights to stay. For budget hotels in Chester, 3 to 4 days should be all the nights you need. That's generally enough to enjoy the city's top attractions, though there's certainly enough to do to warrant a week-long trip.

  3. When booking cheap hotel rooms in Chester, it's typically best to book about 3 weeks in advance. Book further in advance than that and you could be paying too much for your room, as hotels will often overestimate future demand. However, if you wait too long, you might find that the hotel has been completely booked.

  4. When you utilize search filters on Expedia, you'll be able to narrow down your results in a flash. These search filters cover a wide variety of factors you may be interested in when it comes to finding a cheap hotel in Chester, including amenities such as Free Breakfast, 2-star rating, or proximity to local attractions. You can even set filters for price limits to ensure that all the displayed results are within your budget.

Top Chester Hotel Reviews

Frequently asked questions

What is Chester like for travelers on a budget?
Check out cheap places to stay in Chester on Expedia.com and book a trip that stays within your budget. You can scroll through a wide offering of accommodations with Member Prices to find the best deal for you. With our site's handy page filters, you can limit results by your price range, or by amenities that customers often look for like free breakfast and free airport transportation. If you're interested in affordable options near specific attractions, such as Chester Town Hall, try filtering by location to refine your search. As you browse, click the heart button to keep track of your favorites so that you can find them later and make your final decision. Need a car or a flight too? Take a look at the travel packages offered under Bundle and Save and discover more amazing deals by booking transportation at the same time.
When is the best time for a budget trip to Chester?
Weather will likely play an important role when you plan your trip to Chester, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What is there to see and do in Chester?
You don't have to spend a lot to find places to visit in Chester. You can budget for the local attractions that interest you most, and then fill your itinerary with sights that cost very little. Check out the area's cultural spots like Chester Town Hall and Jacob's Pillow, or hunt for bargains with some shopping at Lee Premium Outlets.
How can I get to Chester and get around on a budget?
Scoping out the transportation options in Chester can help keep you on budget. The most convenient airport is 15.4 mi (24.7 km) away from the center in Westfield, MA (BAF-Barnes Municipal). However, if that doesn't suit your budget, you can book a flight to Pittsfield, MA (PSF-Pittsfield Municipal), located 18.9 mi (30.4 km) away. Chester may not have many public transit choices so a car rental could be a reasonable alternative to see more of the area.

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