Where to Stay in the Berkshires, Western Massachusetts

The Red Lion Inn is a mainstay in the Berkshires, and is easily one of the best Berkshires hotels in town. Each room and suite here has a completely unique style; no two are alike! Antiques and charming decor give the feel of having stepped back in time, but modern amenities like fluffy bathrobes and luxurious linens will keep you nice and comfy throughout your Berkshires stay.

The Red Lion Inn is truly a testament to the Gilded Age of luxury. Plus, when you stay here you’re just a few minutes walk to Housatonic River and the iconic Mission House, which you should definitely work into your travel plans. Don’t forget to see what’s on the menu at the Lion’s Den Pub.

The Inn at Stockbridge is another charming area to stay in Stockbridge, full of antique furniture and period details. There are 15 smoke-free guest rooms here, as well as a giant outdoor pool and a fitness room. If you want an upgraded experience, book one of the Barn Suites: you’ll get extra amenities like a working fireplace and a lounge sofa.

Another thing to love about the Inn at Stockbridge—all guests are invited to a wine and cheese reception daily. Oh, there’s also a library and an extensive record collection belonging to the owner. You’ll feel right at home here

The Porches Inn is a must-see when you stay in the Berkshires, even if you don’t end up booking a room. It’s a Berkshire institution, making up a row of 19th-century Victorian houses ringed with (you guessed it) porches. And it’s located right across from Mass MoCA.

The Porches Inn in the Berkshires has just seven rooms, but each with a distinct design and style. Some come with spiral staircases or even fireplaces. There’s also a year-round heated pool, hot tub, sauna, and fire pit to complete your Berkshire getaway.

If you’re looking for hotels in the Berkshires that are more budget-friendly, you can’t go wrong with the Holiday Inn Berkshires. This is one of the most family-friendly places to stay in the Berkshires (kids stay and eat for free), with 90 rooms, a dining room and restaurant, and even free parking.

You’re also close to the town center area when you stay here. The Holiday Inn Berkshires might not be a fancy cottage house, but you’re guaranteed a great travel experience with everything right at your fingertips.

Who doesn’t love a good bed and breakfast? The Harbour House Inn Bed and Breakfast is technically on the outskirts of the park reserve, but it’s one of the nicest inns in the Berkshires area and will complete your Berkshire getaway.

This Georgian Colonial inn welcomes guests with comfortable rooms, dreamy beds, and antique furnishings. Soak up the lush garden with its mountain views and enjoy a homemade breakfast before heading out to travel around the area. You’ll get freshly baked muffins, brewed coffee, and other dishes made from local ingredients to get your day started off right.

Also located in the park reserve area, the owners of this Berkshire property spared no expenses in turning a rustic barn into a comfortable, open-concept vacation home. If you’re not interested in staying in hotels, definitely check out this place.

Wifi, a barbecue grill, a full kitchen and seating area and more are all included here. And yes, this is still a working farm area—you’ll be treated to fresh eggs for breakfast on your visit!

The Seven Hills Inn is one of the best Berkshires hotels in the region. This year-round boutique is set on 27 acres of gardens, making it the ideal Berkshire getaway for anyone (while still being in the heart of Lenox). All the rooms are modern and recently upgraded with plush new bedding, flat-screen TVs, and plenty more.

This Inn is basically a retreat, and an impressive retreat at that. You can stroll the tree-lined lanes, sunbathe, hang out at the pool, see what’s on the breakfast menu, or hang out at the wine bar. The Plunkett Lounge dining room in the main house is the perfect spot to grab a cheese tray (or something else on the menu) while enjoying the Berkshire surroundings.

Complete your stay in the Berkshires with a bit of luxury at the Birchwood Inn—one of the nicest inns in the Berkshires. Believe it or not, it started out as a tavern in the 1700s and now has turned into this Berkshires getaway. Each room is named for a previous owner and is adorned with its own style. And the bed? You’ll find it hard to leave behind.

If your travel plans include the Berkshires, you might as well pamper yourself at a place like this in Lenox. No matter the season, hang out by the fire, order some room service, and enjoy the gardens.

Let’s take a break from all the inns! The Hotel on North is one of the best Berkshires hotels around. It’s smack dab in the middle of all the action, and each room has its own unique style. It’s got a lot of quirky edginess: you can admire all the exposed brick while sipping cocktails in a birdcage elevator, for example. And the restaurant is fantastic.

This hotel has stayed true to its Berkshires heritage while also adding touches of modernity. You’ll get lightning fast wifi, gas fireplaces, wet bars, and more. There’s even a library suite with literally a full library of books.

Last on our list of Berkshires hotels is this fairly affordable inn with basic but comfortable amenities. All rooms here come with plush beds, air conditioning units, wifi, and more. There are a handful of rooms that are also accessible for people with disabilities.

If you want an affordable hotel to stay as you travel around the Berkshires, this is it. There’s lots to see and do right outside the front door, and believe me, the Berkshires do not disappoint. The friendly staff are always on hand to offer additional information before you head out to explore.