Hotels near Chesterwood South Lee

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Top 5 hotels near Chesterwood at a glance

Monument Mountain Motel — 2.5-star hotel in 8.7 km from Chesterwood. Guest rating: 9.0/10 — Wonderful.
Holiday Inn Express Hotel & Suites Great Barrington by IHG — 2.5-star hotel in 8 km from Chesterwood. Guest rating: 8.8/10 — Excellent.
The Inn at Stockbridge — 4-star hotel in 5.2 km from Chesterwood. Guest rating: 9.8/10 — Exceptional.
East Rock Inn — 2-star hotel in 10.1 km from Chesterwood. Guest rating: 9.6/10 — Exceptional.
The Cornell Inn, Lenox & The Berkshires — 3.5-star hotel in 10.7 km from Chesterwood. Guest rating: 9.2/10 — Wonderful.

Where to stay near Chesterwood?

Room, 2 Queen Beds, Non Smoking | Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)

Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)

Monument Mountain Motel

8.7 km from Chesterwood

Dom

CNY577

CNY644 total

includes taxes & fees

Sep 14 - Sep 15

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8 km from Chesterwood

Jennifer

CNY803

CNY897 total

includes taxes & fees

Sep 13 - Sep 14

The Fox Den in the Mainhouse | 1 bedroom, premium bedding, laptop workspace, iron/ironing board

The Inn at Stockbridge

5.2 km from Chesterwood

Stephen

CNY2,543

CNY2,982 total

includes taxes & fees

Sep 13 - Sep 14

Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Classic Double Room, 2 Queen Beds, Courtyard View | Premium bedding, pillowtop beds, in-room safe, blackout drapes

East Rock Inn

10.1 km from Chesterwood

Edward

CNY850

CNY950 total

includes taxes & fees

Sep 9 - Sep 10

The Cornell Inn, Lenox & The Berkshires

10.7 km from Chesterwood

Sherilyn

CNY1,200

CNY1,380 total

includes taxes & fees

Aug 25 - Aug 26

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

14.9 km from Chesterwood

Peter

CNY533

CNY595 total

includes taxes & fees

Sep 13 - Sep 14

Basic Double Room | Blackout drapes, iron/ironing board (on request), WiFi (free)

Sunset Inn

9.1 km from Chesterwood

Michael

CNY668

CNY746 total

includes taxes & fees

Sep 1 - Sep 2

Premium Loft, 1 King Bed | Blackout drapes, WiFi (free), individually decorated

Hideaway Inn Lenox

9.6 km from Chesterwood

Jerome

CNY940

CNY1,050 total

includes taxes & fees

Sep 13 - Sep 14

Holiday Inn & Suites Pittsfield-Berkshires by IHG

19.8 km from Chesterwood

Frank

CNY803

CNY897 total

includes taxes & fees

Sep 13 - Sep 14

Berkshire Travel Lodge

9.7 km from Chesterwood

Michael

CNY455

CNY510 total

includes taxes & fees

Aug 19 - Aug 20

Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk

Quality Inn Great Barrington

10.3 km from Chesterwood

Andrii

CNY625

CNY698 total

includes taxes & fees

Sep 7 - Sep 8

In-room safe, desk, cribs (free), rollaway beds (free)

Suite, 2 Bedrooms, Non Smoking | In-room safe, desk, cribs (free), rollaway beds (free)

Travelodge by Wyndham Great Barrington Berkshires

6.2 km from Chesterwood

Abdul Samad

CNY533

CNY595 total

includes taxes & fees

Sep 1 - Sep 2

One queen bed non smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

One king bed non smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

4.7 km from Chesterwood

Sarah

CNY467

CNY513 total

includes taxes & fees

Aug 19 - Aug 20

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

8.6 km from Chesterwood

Regina

CNY1,313

CNY1,466 total

includes taxes & fees

Aug 27 - Aug 28

Pines Duplex Suite | Premium bedding, laptop workspace, blackout drapes

Inn at Silver Maple Farm

17.5 km from Chesterwood

Linda

CNY1,342

CNY1,503 total

includes taxes & fees

Sep 1 - Sep 2

Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board (on request), cribs (free)

The Little Lion

5.1 km from Chesterwood

Kathryn

CNY759

CNY848 total

includes taxes & fees

Sep 13 - Sep 14

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

In-room safe, desk, laptop workspace, blackout drapes

Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

charles

CNY769

CNY859 total

includes taxes & fees

Aug 30 - Aug 31

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

42-inch flat-screen TV with cable channels, TV

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

14.9 km from Chesterwood

Brian

CNY1,066

CNY1,190 total

includes taxes & fees

Sep 14 - Sep 15

2 full Extra Long Beds | Desk, laptop workspace, WiFi (free)

Berkshire Lake Lodge

16.2 km from Chesterwood

"The phone number for the motel was disconnected. We could not contact the motel. The bathroom was so small even a slender person has to bend and twist to try to shut the door. There was no hairdryer. The sounds of the Thruway required earplugs. They knew we were coming, they could've turned on the AC so that it had fresh air. Although, obviously, great attempts were made to make it cozy and comfortable, it is not suitable for some people."

Laura

CNY1,079

CNY1,205 total

includes taxes & fees

Sep 13 - Sep 14

Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Judy

CNY935

CNY1,044 total

includes taxes & fees

Sep 13 - Sep 14

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Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
Monument Mountain Motel	9.0 Wonderful 896 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	8.8 Excellent 800 reviews	View
The Inn at Stockbridge	9.8 Exceptional 101 reviews	View
East Rock Inn	9.6 Exceptional 53 reviews	View
The Cornell Inn, Lenox & The Berkshires	9.2 Wonderful 1,002 reviews	View

Other landmarks near Chesterwood

Norman Rockwell Museum

9.4/10 (347 reviews)

Norman Rockwell Museum is 0.8 mi (1.2 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Berkshire Botanical Garden, Naumkeag Museum, and National Shrine of the Divine Mercy.

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Berkshire Botanical Garden

9.4/10 (14 reviews)

Ready for an education in local botany? Berkshire Botanical Garden should make your list of places to visit, located 1.2 mi (2 km) from central Stockbridge. Want to stretch your legs some more? Head to Naumkeag Museum and The Mount, both nearby.

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Mission House

9.6/10 (5 reviews)

If museums are on your list of things to see in Stockbridge, then you might want to head to Mission House. If you want to see more of the museums in Stockbridge, Norman Rockwell Museum and Animagic Museum of Animation aren't far.

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Naumkeag Museum

9.4/10 (10 reviews)

If museums are on your list of things to see, then you might want to head to Naumkeag Museum, located in the heart of Stockbridge.If you want to see more of the museums in Stockbridge, you can easily walk to Mission House.

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National Shrine of the Divine Mercy

9.0/10 (83 reviews)

If seeing the sights is on your list of things to do, head to National Shrine of the Divine Mercy— just one of the landmarks located 0.5 mi (0.8 km) from central Stockbridge.

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Schantz Galleries

7.2/10 (5 reviews)

Art fans might want to browse the collections at Schantz Galleries in Stockbridge. If you want to see more of the art galleries in Stockbridge, Norman Rockwell Museum and Art et Industrie aren't far.

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Art et Industrie

8.0/10 (5 reviews)

If you like art, you might want to check out the upcoming exhibitions at Art et Industrie in Great Barrington. If you want to see more of the art galleries in Great Barrington, Norman Rockwell Museum and Schantz Galleries aren't far.

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Berkshire Theatre Festival

8.8/10 (3 reviews)

Berkshire Theatre Festival is 0.9 mi (1.5 km) from central Stockbridge, why not stop by during your stay. If you enjoy the show and want to see another, Tanglewood Music Center and Shakespeare and Company are both not far.

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Frequently asked questions

What are the best hotels near Chesterwood?

Guests love staying at The Inn at Stockbridge, which is a bed & breakfast near Chesterwood.
Another highly rated bed & breakfast is Devonfield Inn B&B, which is a short drive away.
In fact, you'll have plenty of options to choose from with 2,070 hotels, vacation rentals, and other accommodations in the area.

How much does it cost to stay in a hotel near Chesterwood?

You can find the best price for your travel budget on Hotels.com by adding your search criteria and sorting by price. Prices vary based on when and where you plan to go.

Take a look at the lowest price per night from CNY510

What cheap hotels are close to Chesterwood?

For a wallet-friendly hotel close to Chesterwood, Quality Inn Great Barrington is a good option and offers a free on-the-go breakfast, a free daily manager's reception, and free parking.
A second low-cost choice is The Yankee Inn, which is 26 minutes away by car.

Can I find hotels close to Chesterwood that are fully refundable?

Yes, there are many hotels with refundable room rates, but be sure to check the cancellation deadline. Find refundable rates using the "Fully refundable" filter when you search for hotels.

Both The Inn at Stockbridge and Seven Hills Inn are highly rated hotels close to Chesterwood that offer these rates.

What are the best romantic hotels near Chesterwood?

For a romantic stay, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood offers chef service. It's a 14-minute walk from Chesterwood.
The Red Lion Inn is another great choice, and it's a short drive away.

What are the best hotels close to Chesterwood with free breakfast?

Start your day nourished with a free cooked-to-order breakfast at The Inn at Stockbridge, which is a short 10-minute drive from Chesterwood.
Devonfield Inn B&B is also a recommended place to stay with a free full breakfast, and it's located a short drive away.

Which hotels near Chesterwood have rooms with great views?

Travelers can enjoy rooms with garden or pool views at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, which is a 14-minute walk from Chesterwood.
Another great choice nearby is The Inn at Stockbridge, which has rooms with garden or pool views.

What are the best family hotels close to Chesterwood?

Keep the family happy with a stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel which offers free cribs, free parking, and a free continental breakfast. Chesterwood is a short drive away.
Also consider Holiday Inn & Suites Pittsfield-Berkshires by IHG as another great choice for your family's trip.

What are the best luxury hotels near Chesterwood?

Indulge yourself when you stay at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, which is a 14-minute walk from Chesterwood and offers a seasonal outdoor pool and an art gallery.
Another luxe option is Miraval Berkshires Resort & Spa Adults Only, which is a short drive away.

What are the best hotels near Chesterwood with free parking?

Travelers looking to drive and park with ease should consider a stay at The Inn at Stockbridge, which offers free parking. You'll be a short 10-minute drive from Chesterwood.
Devonfield Inn B&B also has free parking and is a short drive away.

What are the best hotels near Chesterwood with a pool?

Travelers can enjoy the seasonal outdoor pool at The Inn at Stockbridge. Chesterwood is a short 10-minute drive from the hotel.
Another great choice for a hotel with a pool is Devonfield Inn B&B.

What cheap motels can I book close to Chesterwood?

To stay economically near Chesterwood, you can book Pleasant Valley Motel West Stockbridge, which offers parking and free in-room WiFi.
The Little Lion is another inexpensive motel to consider in the area.

What are the best things to see and do around my hotel near Chesterwood?

Before or after your visit to Chesterwood, you can check out nearby sights like Tanglewood Music Center, National Shrine of the Divine Mercy, and Norman Rockwell Museum.
Other places in the area are Lee Premium Outlets, Ski Butternut, and The Mount.

What are the best pet-friendly hotels close to Chesterwood?

Bring your furry friend to The Inn at Stockbridge, which is a short 10-minute drive from Chesterwood.
Another pet-friendly spot is Devonfield Inn B&B.