Book Hotels in Cheshire, MA

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Top Cheshire hotels

The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $268 total per night from Oct 27 to Oct 28
$268 total
Oct 27 - Oct 28
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference ...
"Great hotel. Food and drinks were very good. Not much to do in the town but a great place for walking."

Reviewed on Sep 21, 2025

Opens in a new windowThe Williams Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $154 total per night from Sep 28 to Sep 29
$154 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate ...
"The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area ..."

Reviewed on Sep 22, 2025

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from Sep 29 to Sep 30
$143 total
Sep 29 - Sep 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby ...
"Ggg"

Reviewed on Sep 20, 2025

Opens in a new windowBerkshires Untold
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
$115 nightly
The price is $128 total per night from Oct 27 to Oct 28
$128 total
Oct 27 - Oct 28
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
"great location. so nice to wake up to the view of the lake and have kayaks on property to rent. within a short drive of everything. staff was very nice and informative. downsides are you can hear everything through the front door. it’s hard to stay quiet enough for your neighbors. also no water pressure ..."

Reviewed on Sep 22, 2025

Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Sep 28 to Sep 29
$126 total
Sep 28 - Sep 29
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, ...
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."

Reviewed on Sep 25, 2025

Opens in a new windowBerkshire Mountain Lodge
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $241 total per night from Sep 29 to Sep 30
$241 total
Sep 29 - Sep 30
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
"A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops."

Reviewed on Sep 16, 2025

Opens in a new windowThe Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from Sep 28 to Sep 29
$143 total
Sep 28 - Sep 29
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks ...
"Always very relaxing. Kids love the pool and we enjoy the hot tub and views"

Reviewed on Sep 21, 2025

Opens in a new windowVacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $162 total per night from Oct 27 to Oct 28
$162 total
Oct 27 - Oct 28
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...
a gem
"Totally perfect for mass mocha"

Reviewed on Sep 21, 2025

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $110 total per night from Oct 5 to Oct 6
$110 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"

Reviewed on Sep 18, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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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.

Cheshire Hotel & Travel Guide

Within a 6-mile (10-kilometer) distance of the hustle and bustle of Cheshire, with Travelocity's reservations page you can choose from a small, but excellent offering of accommodations. With 4 places to stay on Travelocity within a 6-mile (10-kilometer) sweep of the city center, it shouldn't be hard to find a place suitable.

Travelocity-listed hotels that are located within a short drive of Cheshire include the The Spring's Inn and The Weathervane Motel.

Check out the Rookwood Inn and also the Gateways Inn & Restaurant. The Rookwood Inn is situated 16 miles (25 kilometers) outside of the main part of Cheshire. The Gateways Inn & Restaurant, can be found just 16 miles (25 kilometers) away. The Hampton Terrace Inn along with the Cranwell Spa and Golf Resort are two other Travelocity-listed accommodation options worth looking into in Cheshire.

If you have the time, why not spread your wings and explore the many attractions dotted around Western Massachusetts while you are here? Fall in love with Western Massachusetts's mountains and rolling hills. You should also venture to a few of its history museums. In this area of United States of America adventurous travelers may also enjoy skiing and cross-country skiing.

20 miles (32 kilometers) away from Cheshire, you'll find Lee, where you can spend a few hours exploring Lee Prime Outlets and Tyringham Cobble. When you spend a few nights in Lee, be sure to check out the Black Swan Inn, an Ascend Collection Hotel and Chambery Inn. Alternatively, you could stay in Lenox, 15 miles (24 kilometers) southwest of Cheshire, where you have the options of the Birchwood Inn and Hampton Inn & Suites Berkshires Lenox. The Shakespeare and Company and Tanglewood Music Center are other popular places to check out when in Lenox.

If you are into sports and enjoy attending thrilling games you could spend a day at Times Union Center, which can be found 30 miles (50 kilometers) to the west of Cheshire. Book accommodation right in the thick of the sporting action at the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

Situated 35 miles (57 kilometers) outside Cheshire's center is Albany International Airport. Find nearby rooms at Albany Marriott or Homewood Suites by Hilton Albany.

Top reasons for your vacation to Cheshire

  • Thrilling Skiing Adventures: Cheshire, Massachusetts is a premier destination for family ski vacations. Hit the slopes at local ski resorts and experience the thrill of skiing down snowy mountains.
  • Breathtaking Scenic Lakes: Take in the stunning views of nearby lakes as you ski, creating a picturesque backdrop for your adventures.
  • Tranquil Cheshire Countryside: Embrace the tranquility of nature as you explore the charming Cheshire countryside, surrounded by serene forests and parks.
  • Nearby City Excursions: Visit nearby cities like Pittsfield and North Adams for a change of pace. Enjoy shopping, dining, and immerse yourself in cultural experiences.
  • Cozy Small-Town Vibes: Experience the welcoming atmosphere of Cheshire, a charming small town that offers a perfect blend of outdoor excitement and cozy vibes for a memorable ski vacation.

Find your favorite hotels in Cheshire

If you're planning a ski vacation in Cheshire, Massachusetts, you'll find a variety of hotel accommodations to choose from. Whether you're looking for a cozy lodge, a family-friendly resort, or a luxurious hotel, there are options to suit every traveler's preference. Many hotels in Cheshire offer amenities such as pools, spas, and on-site dining. To make the most of your stay, be sure to check out hotel reviews to find the perfect fit for your family's needs.

Hotel nameTypeStarsDescription
Harbour House InnBed & breakfast3.5This 3.5-star Bed & Breakfast is a great option for your ski vacation in Cheshire, Massachusetts. Located in close proximity to various recreational activities such as horseback riding, fishing, and mountain biking, this hotel offers plenty of opportunities for outdoor adventure. Additionally, its convenient location makes it accessible to the wedding venues, boating facilities, and beautiful gardens in the area. With its free breakfast and no smoking policy, Harbour House Inn ensures a comfortable and enjoyable stay for you and your family.

Explore the best activities and sights in Cheshire

Cheshire, Massachusetts is the perfect destination for a family ski vacation. With its close proximity to family-friendly activities, there's something for everyone to enjoy. Hit the slopes at the local ski resorts and spend quality time together as you glide down the snowy mountains. If skiing isn't your thing, explore the charming town and indulge in some shopping or dining. Take a hike in the nearby forest parks and admire the stunning natural beauty. Don't miss out on the chance to spot wildlife and enjoy the serene lakeside views. Cheshire is the ultimate destination for a memorable family ski vacation.

  1. St Mary's of the Assumption Church: St Mary's of the Assumption Church is a charming point of interest that embodies the beauty of nature and the rich cultural heritage of Cheshire. Situated amidst breathtaking mountains and scenic hiking trails, this church offers a peaceful retreat for visitors seeking a spiritual experience. The serene lake nearby provides a tranquil backdrop, perfect for reflection and contemplation. Additionally, the church is located close to a renowned university, making it an ideal spot for those interested in exploring the academic and intellectual side of the town. Whether you're interested in immersing yourself in nature, attending an opera performance, or simply admiring the picturesque scenery, St Mary's of the Assumption Church promises a unique and unforgettable experience.

Where to stay in Cheshire

Prepare for a delightful ski vacation in Cheshire, Massachusetts, where you and your family can indulge in thrilling activities, breathtaking scenery, and a welcoming small-town atmosphere. As you hit the slopes, take in the stunning views of the nearby scenic lakes, creating a picturesque backdrop for your skiing adventures. Afterward, explore the charming Cheshire countryside and embrace the tranquility of nature. For a change of pace, consider visiting the nearby cities, such as Pittsfield and North Adams, where you can enjoy shopping, dining, and cultural experiences. Cheshire offers the perfect blend of outdoor excitement and cozy small-town vibes for an unforgettable ski vacation.

  1. Lenox: Lenox is a charming city located 15.5 miles away from Cheshire. It is known for its beautiful gardens, museums, and live music scene. Families can explore the rich art and architecture, enjoy hiking in the scenic surroundings, and visit the local library. Lenox offers a unique blend of entertainment and tranquility, making it a perfect destination for a ski vacation with your family.
  2. Pittsfield: Located just 9.1 miles away from Cheshire, Pittsfield is a vibrant city with a rich historical background. It offers a variety of activities for families, including baseball games, sports events, theater performances, and opera shows. Families can also visit museums, enjoy biking around the city, and spend time by the lake. With its proximity to ski resorts, Pittsfield is an excellent choice for a ski vacation with a mix of cultural and outdoor experiences.
  3. Williamstown: Situated 10.6 miles away from Cheshire, Williamstown is a picturesque city known for its university and art scene. Families can explore the museums, go hiking in the nearby mountains, and enjoy ski activities. The city also offers theater performances, a library, and various entertainment options. With its family-friendly atmosphere and stunning scenery, Williamstown is a great choice for a ski vacation that combines cultural experiences with outdoor adventures.

Best times to go to Cheshire

The travel seasons of Cheshire

Trips to Cheshire show a small change in popularity throughout the year. The peak season to visit is from June to August, with July being the highest month. Off-peak season starts from November to January, and December sees the least travelers.

Cheshire has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 67.6 degrees Fahrenheit. The wettest month in Cheshire is July, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January19.9°F (-6.7°C)Light RainMostly Cloudy
February22.1°F (-5.5°C)Light RainMostly Cloudy
March29.7°F (-1.3°C)Light RainMostly Cloudy
April41.4°F (5.2°C)Light RainMostly Cloudy
May53.8°F (12.1°C)Light RainMostly Sunny
June61.5°F (16.4°C)Light RainMostly Sunny
July67.6°F (19.8°C)Light RainMostly Sunny
August65.7°F (18.7°C)Light RainMostly Sunny
September58.6°F (14.8°C)Light RainMostly Sunny
October47.7°F (8.7°C)Light RainMostly Cloudy
November35.4°F (1.9°C)Light RainMostly Sunny
December27.0°F (-2.8°C)Light RainMostly Cloudy

How do I find a great hotel with Travelocity?

Ensure your whole crew enjoys an unforgettable vacation. Utilize our family-friendly badge to find hotels that offer extra amenities for children. Take advantage of our custom filters to narrow down options, choosing hotels closest to popular attractions, with enhanced cleaning measures, and within your budget. Trust our reliable online travel platform for a seamless booking experience.

Why should I book with Travelocity?

Conference calls, to-do lists, and, of course, football practice. Busy lives and packed schedules call for hassle-free trips. Our aim is to provide worry-free travel every time you and your family book with us, so you can spend less time fretting and more time creating cherished memories. With our assistance, you can discover and plan your ideal journey, benefiting from transparent pricing, reliable reviews, and 24/7 guaranteed customer support before, during, and after your vacation.

How can I save money on my trip to Cheshire?

Avoid the peak season from June to August when planning your trip to Cheshire. This is when prices are higher and attractions are more crowded. To save money, consider bundling your flights, hotel, and car bookings as a package deal. Three inexpensive activities you can enjoy in Cheshire are hiking in the beautiful nature trails, exploring the local shops for budget-friendly shopping, and taking your family for a picnic by the serene lakeside.

Frequently asked questions

What are the top kid-friendly hotels in Cheshire?
Take some of the worries out of traveling with little ones by booking a family-friendly Cheshire hotel. From thoughtful amenities to additional services, these properties feature perks that'll help make your getaway run like a dream: 19th c. Barn in the Berkshires will help make your next trip the most memorable one yet. It features a range of conveniences geared toward families, such as a playground and animal viewing activities. Harbour House Inn is another great choice. After a long day of exploring, return to your comfortable room and amenities like complimentary breakfast and free WiFi.
Where can I find cheap hotels in Cheshire?
At Travelocity you'll find really nice hotels in Cheshire at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Cheshire rather than in Cheshire. We may find you even better rates, too.
How do I find the best Cheshire hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Cheshire then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Cheshire?
The cheapest hotel in Cheshire is $110. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Cheshire?
There are 997 hotels in Cheshire on Travelocity.
What are the best hotels in Cheshire?
Cheshire has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Cheshire for you!
When is the best time to visit Cheshire?
If you want the joy of a fun-filled trip in peak season, visit Cheshire during June, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Cheshire?
Based on historic data is usually the cheapest month to visit Cheshire. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Cheshire?
There are multiple hotels in Cheshire that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Cheshire. We have plenty of kid-friendly hotels in Cheshire to choose from on Travelocity!
Why book a hotel in Cheshire through Travelocity?
Because we have the top hotels in Cheshire! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Cheshire on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Cheshire hotel reviews by fellow wanderers

Berkshire Mountain Lodge

Berkshire Mountain Lodge

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. "
A verified traveler from Weymouth stayed at Berkshire Mountain Lodge
Berkshire Mountain Lodge
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