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Courtesy of The Porches Inn at MASS MoCA

Western Massachusetts: The 12 best places to stay

From Gilded Age mansions to country inns, 12 fantastic options for your next trip

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It’s easy to be overwhelmed by the abundance of places to stay when you’re ready to explore the natural beauty and charming small towns of Western Massachusetts.

The region is typically linked in travelers’ minds with cute bed and breakfasts or cottages, but don’t overlook the historic mansions and more modern retreats.

We’ve made it easier to start planning that trip by gathering some of the most interesting and quirky home bases to choose from in Western Mass. and just over the I-91 border.

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1. Wheatleigh

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Hawthorne Rd
Lenox, MA 01240
(413) 637-0610
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Overlooking the Berkshire Mountains on 22 acres that Frederick Law Olmsted designed, it’s easy to forget the rest of the world.

At Wheatleigh, built in the style of a Florentine palazzo, the classic Berkshires rural minimalism is nowhere to be found. Instead, enjoy the terrace suite for the country luxury house experience.

Courtesy of Wheatleigh

2. The Inn at Stockbridge

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30 East St
Stockbridge, MA 01262
(413) 298-3337
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Take advantage of the home-cooked, farm-to-table breakfast available each morning at this Georgian-style mansion, and stop by the nightly wine and cheese hour. For a relaxing day before exploring the Berkshires, find the on-call massage therapist and the heated pool.

If you’re looking for a unique stay, rent one of the barn suites, each named after famous artists who influenced the region. The Rockwell suite features rustic decor and a deck, for instance.

3. Kemble Inn

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2 Kemble St
Lenox, MA 01240
(413) 637-4113
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Yes, another Gilded Age mansion, but Kemble’s modern interior makes it uniquely appealing as a retreat to Western Mass.

The intimate lounge and private dining rooms have the best of the classic bed-and-breakfast experience, but the space of the mansion gives guests privacy and luxury.

Hotel staff will even make you a picnic lunch you can enjoy on the grounds.

Courtesy of Kemble Inn

4. Black Swan Inn, an Ascend Collection Hotel Member

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435 Laurel St
Lee, MA 01238
(413) 243-2700
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The Black Swan Inn offers picturesque mountain and lake views, but the real appeal lies in its outdoor activities: Its location on Laurel Lake gives visitors easy access to pontoon boats, paddle boats, and kayaks from the inn.

If you can’t get enough of the lake, reserve a room with a private balcony and view.

For dinner, check out Mint Indian Lakeside Dining, located on-site. 

5. Blantyre

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16 Blantyre Rd
Lenox, MA 01240
(844) 881-0104
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An ivy-covered Gilded Age mansion, Blantyre is the place to go for Western Mass. luxury.

The 110 acres of woodlands give you outdoor options, but don’t skip out on trying the spa, with facials, a vitality bar, and more.

Highly rated food options on-site make staying in tempting—you can choose from three dining experiences featuring live music. If you’re celebrating, don’t miss the Champagne Salon, where you can sit in the garden.

For stays, choose from the more upscale manor house, rustic carriage house, or private cottages.

Courtesy of Blantrye Resort and Estate

6. Eastover Estate & Eco-Village

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430 East St
Lenox, MA 01240
(866) 264-5139
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Sitting on 600 acres in Lenox, Eastover offers the perfect eco-friendly retreat in the Berkshires.

The estate claims to guide guests to “achieve optimal physical and mental states of being” through offerings of yoga studios, meditation rooms, cooking classes, and serene outdoor spaces. Massage therapy options on site can complete your relaxing weekend.

The estate comprises several buildings, from a classic mansion to the contemporary ranch house, with cabin options for larger groups.

7. Hotel on North

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297 North St
Pittsfield, MA 01201
(413) 358-4741
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The Hotel on North is a quirky, modern take on the Western Mass. experience. You’ll notice the unique character of the place right away, from the birdcage elevator converted into a cocktail table to the rotating art exhibit located off the lobby.

No two guest rooms are exactly the same. Designs vary, but the library suite is promising, with 125 bookshelves and a rolling library ladder a la Beauty and the Beast. A claw-foot tub and mountain views add extra luxury.

If you visit during apple-picking season, check out its “peak pick” package for an apple dessert and offerings from a local winery.

8. The Porches Inn at MASS MoCA

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231 River St
North Adams, MA 01247

This retro inn with a self-described “industrial granny-chic decor” is an inviting home base for the North Adams area.

Located across the street from the Massachusetts Museum of Contemporary Art (MASS MoCA), its restored Victorian row homes once housed local mill workers.

Decor remains mostly true to the period, with vintage lamps and antique plates adorning the walls, mixed in with modern amenities like Apple TVs. The pop-up bar as you enter serves local beers and wines, which you can enjoy on the namesake porches.

Finally, don’t miss the 24/7 pool and hot tub.

Courtesy of The Porches Inn at MASS MoCA

9. Starlight Llama Solar Bed & Breakfast

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940 Chesterfield Rd
Florence, MA 01062
(413) 584-1703
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A working llama farm isn’t the obvious choice for a hospitality escape, but Starlight offers an interesting alternative to the usual weekend away.

The building is fully solar-powered, and on-site meals highlight ingredients grown on the farm. During your stay, you can explore the 120-acre property that was formerly a dairy farm.

From the windows of the white room, one of three rentals, you can see the llamas, emus, and chickens. Don’t miss the friendly miniature Mediterranean donkey, Pedro.

If you tire of admiring the wildlife or just want some solitude, hike through the woods to the historically accurate replica of Henry David Thoreau’s cabin.

Courtesy of Starlight Llama Solar Bed & Breakfast

10. The Hotel Northampton

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36 King St
Northampton, MA 01060
(413) 584-3100
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Located in the center of downtown Northampton, this cozy hotel has been in operation since 1927.

The colonial revival style is inspired by the 18th-century Wiggins Tavern (try its baked stuffed shrimp, which it claims to have invented!).

You’ll be in good company, too—four former presidents spent time here. If you stop by, be sure to check out the Botanic Garden of Smith College and the Museum of Art, both only a half mile away.

11. The Old Mill Inn

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9732, 87 School St
Hatfield, MA 01038
(413) 247-3301
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Furnished in the style of a classic country house, the Old Mill Inn is an idyllic place to stay as you take in the foliage of the Pioneer Valley.

The Inn offers nine different themed rooms decorated for their namesakes, like the Blue Bedroom, named for the portrait of a woman in blue that hangs on the wall. All rooms come with cable, private bathrooms, and Wi-Fi.

For longer stays, check out the vintage industrial decor of the Miller Suite in a studio-apartment style that maintains the original open floorplan. Before you leave, be sure to spend a few minutes admiring the frog pond and listening to the rushing falls of the Mill River.

12. Deerfield Inn

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81 Old Main St
Deerfield, MA 01342
(413) 774-5587
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The Deerfield Inn has operated as a hotel since 1884, when guests arrived in carriages and on horseback. Although today the inn is updated with a modern feel, there are still traces of that past all around.

The carriage house and stables still bear the names of horses kept at the inn during the 19th century.

Today, this charming lodge has 24 rooms between the main inn and the carriage house. There’s also an on-site restaurant and tavern, Champney’s, whose “field to fork” philosophy highlights local ingredients.

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1. Wheatleigh

Hawthorne Rd, Lenox, MA 01240
Courtesy of Wheatleigh

Overlooking the Berkshire Mountains on 22 acres that Frederick Law Olmsted designed, it’s easy to forget the rest of the world.

At Wheatleigh, built in the style of a Florentine palazzo, the classic Berkshires rural minimalism is nowhere to be found. Instead, enjoy the terrace suite for the country luxury house experience.

Hawthorne Rd
Lenox, MA 01240

2. The Inn at Stockbridge

30 East St, Stockbridge, MA 01262

Take advantage of the home-cooked, farm-to-table breakfast available each morning at this Georgian-style mansion, and stop by the nightly wine and cheese hour. For a relaxing day before exploring the Berkshires, find the on-call massage therapist and the heated pool.

If you’re looking for a unique stay, rent one of the barn suites, each named after famous artists who influenced the region. The Rockwell suite features rustic decor and a deck, for instance.

30 East St
Stockbridge, MA 01262

3. Kemble Inn

2 Kemble St, Lenox, MA 01240
Courtesy of Kemble Inn

Yes, another Gilded Age mansion, but Kemble’s modern interior makes it uniquely appealing as a retreat to Western Mass.

The intimate lounge and private dining rooms have the best of the classic bed-and-breakfast experience, but the space of the mansion gives guests privacy and luxury.

Hotel staff will even make you a picnic lunch you can enjoy on the grounds.

2 Kemble St
Lenox, MA 01240

4. Black Swan Inn, an Ascend Collection Hotel Member

435 Laurel St, Lee, MA 01238

The Black Swan Inn offers picturesque mountain and lake views, but the real appeal lies in its outdoor activities: Its location on Laurel Lake gives visitors easy access to pontoon boats, paddle boats, and kayaks from the inn.

If you can’t get enough of the lake, reserve a room with a private balcony and view.

For dinner, check out Mint Indian Lakeside Dining, located on-site. 

435 Laurel St
Lee, MA 01238

5. Blantyre

16 Blantyre Rd, Lenox, MA 01240
Courtesy of Blantrye Resort and Estate

An ivy-covered Gilded Age mansion, Blantyre is the place to go for Western Mass. luxury.

The 110 acres of woodlands give you outdoor options, but don’t skip out on trying the spa, with facials, a vitality bar, and more.

Highly rated food options on-site make staying in tempting—you can choose from three dining experiences featuring live music. If you’re celebrating, don’t miss the Champagne Salon, where you can sit in the garden.

For stays, choose from the more upscale manor house, rustic carriage house, or private cottages.

16 Blantyre Rd
Lenox, MA 01240

6. Eastover Estate & Eco-Village

430 East St, Lenox, MA 01240

Sitting on 600 acres in Lenox, Eastover offers the perfect eco-friendly retreat in the Berkshires.

The estate claims to guide guests to “achieve optimal physical and mental states of being” through offerings of yoga studios, meditation rooms, cooking classes, and serene outdoor spaces. Massage therapy options on site can complete your relaxing weekend.

The estate comprises several buildings, from a classic mansion to the contemporary ranch house, with cabin options for larger groups.

430 East St
Lenox, MA 01240

7. Hotel on North

297 North St, Pittsfield, MA 01201

The Hotel on North is a quirky, modern take on the Western Mass. experience. You’ll notice the unique character of the place right away, from the birdcage elevator converted into a cocktail table to the rotating art exhibit located off the lobby.

No two guest rooms are exactly the same. Designs vary, but the library suite is promising, with 125 bookshelves and a rolling library ladder a la Beauty and the Beast. A claw-foot tub and mountain views add extra luxury.

If you visit during apple-picking season, check out its “peak pick” package for an apple dessert and offerings from a local winery.

297 North St
Pittsfield, MA 01201

8. The Porches Inn at MASS MoCA

231 River St, North Adams, MA 01247
Courtesy of The Porches Inn at MASS MoCA

This retro inn with a self-described “industrial granny-chic decor” is an inviting home base for the North Adams area.

Located across the street from the Massachusetts Museum of Contemporary Art (MASS MoCA), its restored Victorian row homes once housed local mill workers.

Decor remains mostly true to the period, with vintage lamps and antique plates adorning the walls, mixed in with modern amenities like Apple TVs. The pop-up bar as you enter serves local beers and wines, which you can enjoy on the namesake porches.

Finally, don’t miss the 24/7 pool and hot tub.

231 River St
North Adams, MA 01247

9. Starlight Llama Solar Bed & Breakfast

940 Chesterfield Rd, Florence, MA 01062
Courtesy of Starlight Llama Solar Bed & Breakfast

A working llama farm isn’t the obvious choice for a hospitality escape, but Starlight offers an interesting alternative to the usual weekend away.

The building is fully solar-powered, and on-site meals highlight ingredients grown on the farm. During your stay, you can explore the 120-acre property that was formerly a dairy farm.

From the windows of the white room, one of three rentals, you can see the llamas, emus, and chickens. Don’t miss the friendly miniature Mediterranean donkey, Pedro.

If you tire of admiring the wildlife or just want some solitude, hike through the woods to the historically accurate replica of Henry David Thoreau’s cabin.

940 Chesterfield Rd
Florence, MA 01062

10. The Hotel Northampton

36 King St, Northampton, MA 01060

Located in the center of downtown Northampton, this cozy hotel has been in operation since 1927.

The colonial revival style is inspired by the 18th-century Wiggins Tavern (try its baked stuffed shrimp, which it claims to have invented!).

You’ll be in good company, too—four former presidents spent time here. If you stop by, be sure to check out the Botanic Garden of Smith College and the Museum of Art, both only a half mile away.

36 King St
Northampton, MA 01060

11. The Old Mill Inn

9732, 87 School St, Hatfield, MA 01038

Furnished in the style of a classic country house, the Old Mill Inn is an idyllic place to stay as you take in the foliage of the Pioneer Valley.

The Inn offers nine different themed rooms decorated for their namesakes, like the Blue Bedroom, named for the portrait of a woman in blue that hangs on the wall. All rooms come with cable, private bathrooms, and Wi-Fi.

For longer stays, check out the vintage industrial decor of the Miller Suite in a studio-apartment style that maintains the original open floorplan. Before you leave, be sure to spend a few minutes admiring the frog pond and listening to the rushing falls of the Mill River.

9732, 87 School St
Hatfield, MA 01038

12. Deerfield Inn

81 Old Main St, Deerfield, MA 01342

The Deerfield Inn has operated as a hotel since 1884, when guests arrived in carriages and on horseback. Although today the inn is updated with a modern feel, there are still traces of that past all around.

The carriage house and stables still bear the names of horses kept at the inn during the 19th century.

Today, this charming lodge has 24 rooms between the main inn and the carriage house. There’s also an on-site restaurant and tavern, Champney’s, whose “field to fork” philosophy highlights local ingredients.

81 Old Main St
Deerfield, MA 01342