Cheshire Massachusetts is beautiful and has lots of hotels. Ofcourse we are only looking for the best hotels in Cheshire Massachusetts. It’s important to compare them because there are so many places to stay in Cheshire Massachusetts. You’re probably wondering where to stay in Cheshire Massachusetts. To see which hotel sounds better than the other, we created a top 10 list. The list will make it a lot easier for you to make a great decision. We know you only want the best hotel and preferably something with a reasonable price.

Our list contains 10 hotels of which we think are the best hotels in Cheshire Massachusetts right now. Still, some of you are more interested in the most popular hotels in Cheshire Massachusetts with the best reviews, and that’s completely normal! You can check out the link below.

Skip to the most popular hotels in Cheshire Massachusetts.

10 Best Hotels In Cheshire Massachusetts:

  1. Lanesboro Country Inn

    Hotels In Cheshire Massachusetts

    Description:

      Lanesboro Country Inn is located in Lanesborough, just 28 miles from Albany.Some units have a sitting area for your convenience. You will find a coffee machine in the room. The rooms come with a private bathroom. A flat-screen TV with satellite channels is provided.Adams is 9 miles from Lanesboro Country Inn, and Lenox is 12 miles away. The nearest airport is Albany International Airport, 33 miles from the property.

    Reviews:

    • The cabin was cozy with ample sleeping space and adjacent parking.
    • This is our fourth year coming to this property and we have chosen it for location and for pet-friendliness (although this time we didn’t bring a pet). The first year we were in the motel part and we have been in the cabins since. This year we booked for the motel because the cabin was insanely expensive, but the motel room had many problems (most notably the mattress) so they put us in a cabin since the other motel rooms were booked up. The location is fantastic. Super close to the lakes, to Pittsfield, to highways, to ski areas, and especially walkable to a post office, Dollar General, and most importantly, to Krispy Kones with the best wings in the area. Also close to other eating locations. Parking is super easy, right in front of or next to your place. There are grills in the center of it. The staff is friendly, the cabins are adorable and wonderful, and pet friendly – even if you have two dogs. Even if you have a Saint Bernard. We will continue to come here.
    • I liked the fact that there was a kitchen, and that most things appeared to be clean and well presented. The cabin was cozy and well appointed.
    • We were in a quaint, quite spacious log cabin with a king bed, full kitchen facilities, and full bathroom with a jetted tub/shower. It was clean and the bed was comfortable. It was quiet and peaceful, even though Route 7 was quite close and busy. The staff was friendly and there was no problem with our reservations. It suited us and our friends as a nice place to have a quiet “get-away,” but still with easy access to restaurants and other places, including Tanglewood.
    • I was there with my grand kids for the second time now . We felt so comfortable. It was like a home away from home. We will be back in the area the same time next year for Berkshire Geobash and plan to stay again

    For more info click here.

    BOOKING.COM

  1. The Springs Inn

    Hotels In Cheshire Massachusetts

    Description:

      Showcasing a seasonal outdoor pool and views of the mountains, The Springs Inn is located in New Ashford in the region of Massachusetts, just 26 miles from Albany. Free private parking is available on site.All rooms include a flat-screen TV. Certain rooms have views of the pool or garden. Each room is fitted with a private bathroom.There is a shared lounge at the property.There are lots of activities in the area, such as skiing and biking. Adams is 7 miles from The Springs Inn, and Lenox is 16 miles from the property. Albany International Airport is 30 miles away.

    Reviews:

    • A nice little touch was that they left snacks, plates, bowls, and plasticware in the room. They came in handy!!
    • The room was warm when we arrived, and the key was under the mat as promised.
    • They were great and when arriving after 8 and leaving early morning
    • Nice staff clean rooms inexpensive nice with refrigerator location
    • limited breakfast was ok. Location easy to get to.

    For more info click here.

    BOOKING.COM

  1. Berkshire Valley Inn

    Hotels In Cheshire Massachusetts

    Description:

      Located in North Hancock in the region of Massachusetts, 24 miles from Albany, Berkshire Valley Inn features a seasonal outdoor pool and views of the mountains.Each room is fitted with a flat-screen TV with satellite channels. Certain accommodations feature a sitting area to relax in after a busy day. All rooms are fitted with a private bathroom. Extras include free toiletries and a hairdryer.You will find luggage storage space at the property.Adams is 9 miles from Berkshire Valley Inn, and Lenox is 17 miles from the property. The nearest airport is Albany International Airport, 28 miles from the property.

    Reviews:

    • The inn was great , close to the mountain ,breakfast was delicious and the staff was super friendly . Definitely going back !
    • Beautiful setting in the Berkshire Valley. Friendly helpful staff. Geared more for winter but was still somewhere we could sit out in the Autumn sun. Really pretty spot.
    • The bed was very comfy, bathroom clean linens and towels very clean ! The room was older with painted paneling and older styled beaureaus but all were clean . The continental breakfast was very nice. Fresh fruit bowl, variety of breads and bagels, cold and hot cereals, delicious egg cups.coffee , juices. The staff was very friendly and helpful.
    • Large room, friendly staff, clean, includes bath, good value for the money we paid.
    • Charming traditionnel motel renovated, very quiet, close to Williamstown

    For more info click here.

    BOOKING.COM

  1. Yankee Suites Extended Stay

    Hotels In Cheshire Massachusetts

    Description:

      Located in Pittsfield, 29 miles from Albany, Yankee Suites Extended Stay features air-conditioned rooms with free WiFi throughout the property.All rooms are fitted with a flat-screen TV with cable channels and DVD player. A balcony or patio are featured in certain rooms. Every room is fitted with a private bathroom equipped with a bathtub. Extras include free toiletries and a hairdryer.Adams is 14 miles from Yankee Suites Hotel, and Lenox is 6 miles away. The nearest airport is Albany International Airport, 35 miles from the property.

    Reviews:

    • Spacious – the entire apartments and size of rooms including bathroom
      Very clean
      Loved the full kitchen
      Loved the location – walked to a wonderful dinner
      Great value
    • It was clean, comfortable and nicely laid out. The hotel is within 2 blocks of most things you would want to do in Pittsfield
    • The staff was very helpful to me. I had a lot of questions and they answered them with patience and professionalism.
    • We have the amenities of the kitchen, living space and dining room.
    • Staff was very helpful. Apartment comfortable, conveniently located and relatively well stocked. Would stay here again.

    For more info click here.

    BOOKING.COM

  1. Hotel on North

    Hotels In Cheshire Massachusetts

    Description:

      Located in Pittsfield, 29 miles from Albany, Hotel on North features a restaurant, bar and free WiFi throughout the property. Free private parking is available on site.Every room at this hotel is air conditioned and features a flat-screen TV. Every room is equipped with a private bathroom. For your comfort, you will find bathrobes and slippers.You will find a 24-hour front desk and gift shop at the property.Adams is 14 miles from Hotel on North, and Lenox is 7 miles away. Albany International Airport is 35 miles from the property.

    Reviews:

    • Very unique hotel. The rooms are large, spacious and the decor is well thought out. Certainly, this is not a typical hotel. You will actually enjoy spending time in your room, the hotel common spaces, and especially the restaurant. It was homey, comfortable, and the service was excellent.
    • Great location, wonderful bar/ restaurant on site. Hotel is blend of old and new, tin ceilings and great modern plumbing. Front desk staff were knowledgeable and cheerful. Place VERY clean
    • Location was perfect. Attached restaurant was excellent, although service was slow.
    • turndown service included delicious chocolates. Great common spaces. Huge room.
    • Beautiful aesthetic throughout the hotel. Wonderful bed and room amenities. Excellent breakfast!

    For more info click here.

    BOOKING.COM

  1. Berkshire Plaza

    Hotels In Cheshire Massachusetts

    Description:

      Next to the Beacon Cinema in Pittsfield, Massachusetts, this hotel provides guest rooms with free wired internet access and coffee makers as well as an on-site restaurant.Crowne Plaza Pittsfield-Berkshires features an indoor pool and hot tub. Guests can take advantage of the on-site fitness center, then relax in the sauna. A day spa is also on site.Guests can enjoy regional cuisine in the hotel’s restaurant, open for breakfast, lunch and dinner. The Undergound Pub is an English-style pub with live entertainment and over 100 unique beers.The guest rooms at the Pittsfield Crowne Plaza offer unique sleep amenities such as a sleep CD, eye mask and ear plugs. Guests can also enjoy in-room CD players and pay-per-view movies.This hotel is 17 miles from the Berkshire Prime Outlet Village and access to the Appalachian Trail. The Norman Rockwell Museum is 13 miles away.

    Reviews:

    • The pool is wonderful, large and warm. The staff is very attentive.
    • The facility is dated, yet clean. The staff were very nice, but the parking garage was a nightmare. Run down and half of it was crumbling or falling apart. The elevators made horrific noises and were in tough shape. The location is perfect if you have business downtown. The local restaurants are top notch. The breakfast buffet in the hotel was what you would expect from a hotel buffet breakfast. Powdered eggs and overcooked french toast. Pricey for the quality.
    • The kind sized bed was great and the gentleman who worked the front desk- who is ALWAYS- there on Christmas for the past two years, is always fantastic.
    • Parking was free and easy – room was clean and decent.
    • We liked the view that we were in to see the city and the pool/hot tub was nice and clean. The front desk staff was friendly and easy to work with.

    For more info click here.

    BOOKING.COM

  1. Holiday Inn Berkshires

    Hotels In Cheshire Massachusetts

    Description:

      Steps from the Massachusetts Museum of Contemporary Art and placed in downtown North Adams, this hotel offers a spacious on-site health club and easy access to local attractions.Guests at the Holiday Inn Berkshires can start the day with a cup of coffee from in-room coffeemakers and a free weekday newspaper, delivered to each guestroom. The hotel also provides free wireless internet access along with an indoor pool, sauna and fitness center.A variety of recreational activities including skiing and snow boarding are available at nearby Jiminy Peak. The Berkshires Holiday Inn is also a short distance from Heritage State Park and a number of local shopping centers.

    Reviews:

    • A good, serviceable hotel located very conveniently for walking to MassMOCA and North Adams restaurants and shops.
    • Friendly and helpful staff. Changed our room for us as we had been placed near ice-machine, which was v. noisy
    • Front desk upon check-in was very friendly on Sunday. On Monday I spoke to the manager a very gregarious friendly lady named Walton who listened to my concerns about the previous night’s stay and reduced $30 off my bill. This gesture was unsolicited and will have me visit the establishment another time to give it another chance.
    • The hotel was comfortable and clean. The breakfast servings were so large we had leftovers the next morning. We were with a large group that booked another nearby property, that was very expensive. We weren’t going to spend much time in the room, so we decided to save the money. The rest of our group commented that the other property in town was average at best, and they wished they had booked with us at Holiday Inn Berkshires. It was a much better value for the money. Our friends paid $450 more than we did for 3 nights. The Holiday Inn was a fine property with beautiful views, and right in downtown.
    • Located down town,and near the person I was there to see.

    For more info click here.

    BOOKING.COM

  1. 1896 House Country Inn – Brookside & Pondside

    Hotels In Cheshire Massachusetts

    Description:

      Featuring free WiFi and a seasonal outdoor pool, 1896 House Country Motel offers accommodations in Williamstown. Guests can enjoy the on-site bar.Every room at this inn is air conditioned and has a flat-screen TV with cable channels. Certain accommodations include a sitting area for your convenience. Each room is fitted with a private bathroom fitted with a bathtub or shower. For your comfort, you will find free toiletries and a hairdryer.There is business center at the property.A range of activities are available in the area, such as skiing and hiking. Albany is 27 miles from 1896 House Country Motel, and Adams is 7 miles away. The nearest airport is Albany International Airport, 29 miles from 1896 House Country Motel.

    Reviews:

    • The beds were softer than most motel beds, and the bathroom was super with extra-large size and a great shower. The breakfast was very inclusive, with my favorite chia seeds at the cereal bar.
    • Great spot for a New England foliage trip. Restaurants are plentiful and near by. Only minutes from Williams College and MoCA. Easter Egg: There’s a great sitting area at the duck pond out back!
    • the grounds were simply relaxing, we enjoyed walking over the footbridge to get to breakfast. Staff was very polite and helpful
    • It is located close to the very nice path that leads to Clark Art Institute. Breakfast is nice and people working there are very helpful. It is very close to the center of Williamstown.
    • This was an excellent stay — room was large, clean and comfortable. We liked the location, just outside of town with an onsite bar and restaurant. Staff throughout was terrific.

    For more info click here.

    BOOKING.COM

  1. 1896 House Country Inn – Barnside Inn

    Hotels In Cheshire Massachusetts

    Description:

      In Williamstown, the 1896 House Luxury Inn Williamstown is a 5 minute drive from Williams College. The bed and breakfast has an outdoor pool available across from the property and rooms have a spa bathtub.The on-site restaurant and bar is ‘6 House Pub. Guests dining there can enjoy a menu of sandwiches, seafood, pasta and other dishes for lunch and dinner.The rooms are all decorated with unique furniture and style. A fireplace, cable TV and private entrance are some of the amenities included in each room.The 1896 House is a 5 minute drive from the Clark Art Institute and is 10 miles from skiing on Jiminy Peak.

    Reviews:

    • Love the babbling brook and the walkway over it to the restaurant. Liked the discount on dinner- it was delicious and a neat venue.
      Love the old style motel revamped and spotless with rocking chairs on the porches. Knotty pine is always neat!
    • We have stayed several times before and have always been satisfied. This was the first time staying in one of the suites, which was quite spacious and comfortable, but they could have done more with the space in the bathroom, e.g., a larger shower and double sinks.
    • Lovely, if a bit over-decorated, suite and pretty grounds.
    • Nice setting. Comfortable spacious room decorated with period furniture. Wonderful breakfast with private cook was unique!
    • Amazing!!! Huge rooms, awesome full breakfast included and pub/restaurant right next door!!! Very clean!!!

    For more info click here.

    BOOKING.COM

  1. The Porches Inn at Mass MoCA

    Hotels In Cheshire Massachusetts

    Description:

      Located across from the Massachusetts Museum of Contemporary Art, this inn offers on-site art exhibitions and an outdoor pool with heated pool deck. Mount Greylock is 8 miles away.The Porches Inn at Mass MoCA features guest rooms decorated in retro-style furnishings and bright colors.The unique rooms all include free Wi-Fi access, a minibar, and flat-screen TV. They have plush bathrobes and a private bathroom.Guests can work out in the fitness center and relax in the sauna and hot tub.The Lobby Bar offers full bar service in a relaxed atmosphere. A continental breakfast is offered daily, and room service with boxed lunches is available.Various New Adams art galleries are a 15 minute walk away. Desperado’s Mexican Restaurant and Big Shirl’s Kitchen are both 2 miles from the Porches Inn.

    Reviews:

    • Comfortable beds and crisp linens & duvets…..excellent service!
    • Porches Inn is right across the street from Mass MoCA, and a few blocks from restaurants and galleries. Also, the complimentary breakfast was great!
    • Warm & inviting spaces offered a relaxing experience.
    • Room was super comfortable and I loved the bathroom.
    • We were given a ground floor room at the rear of the property, so there was no traffic noise, and the room was big and adequately equipped.
      The room was clean and bed (a Queen) was comfortable enough.
      The location of the Inn was good – MassMoCa is within a few minutes walk, and other amenities and restaurants are reachable on foot.

    For more info click here.

    BOOKING.COM

Top Hotels In Cheshire Massachusetts Conclusion:

The above is a top selection of the best hotels to stay in Cheshire Massachusetts to help you with your search. We know it’s not that easy to find the best hotel because there are just so many places to stay in Cheshire Massachusetts but we hope that the above-mentioned tips have helped you make a good decision.

We also hope that you enjoyed our top ten list of the best hotels in Cheshire Massachusetts. And we wish you all the best with your future stay!

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