Find hotels near Chesterwood, South Lee from SAR 249

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
28 Rab. II - 29 Rab. II
Tomorrow
29 Rab. II - 30 Rab. II
This weekend
2 Jum. I - 4 Jum. I
Next weekend
9 Jum. I - 11 Jum. I

Filter by

Guest rating
Guest rating
Star rating

Compare 729 hotels close to Chesterwood with room rates, reviews, and availability. Most hotels are fully refundable.

Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is SAR 822
SAR 822 total
includes taxes & fees
30 Apr - 1 May
Tanglewood Suites
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (124)
"Very enjoyable comfortable stay"
The price is SAR 934
SAR 1,043 total
includes taxes & fees
30 Apr - 1 May
Devonfield Inn B&B
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is SAR 840
SAR 939 total
includes taxes & fees
6 May - 7 May
Granville House
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1002)
"We had a wonderful wknd in Lenox. The Cornell Inn was very accommodating and everyone was extremely friendly, welcoming and helpful. We had emailed beforehand about dietary restrictions and they were helpful and gave great recommendations for places that could accommodate us. Their breakfasts are excellent and filling. That starts your day off so nicely. The rooms were comfortable and roomy. Although the room was a bit dated -it was cozy and suited us perfectly. It was a great location...
The price is SAR 533
SAR 742 total
includes taxes & fees
30 Apr - 1 May
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Quaint & hospitable!"
The price is SAR 559
SAR 792 total
includes taxes & fees
30 Apr - 1 May
The Red Lion Inn
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is SAR 866
SAR 967 total
includes taxes & fees
1 May - 2 May
Brook Farm Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (697)
"Stayed a week while working in the area. Staff was super friendly, rooms were clean & quiet, mattresses pretty comfortable. The only thing keeping it from a solid 5 stars was the breakfast is not so good. Watery eggs just aren't my jam. "
The price is SAR 566
SAR 633 total
includes taxes & fees
26 May - 27 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
East Rock Inn
Exterior

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (24)
"The property is well maintained and set back from the road. It was very quiet and the rooms are fantastic. A must stay if you are going to be in the area. "
The price is SAR 456
SAR 509 total
includes taxes & fees
1 May - 2 May
East Rock Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is SAR 713
SAR 796 total
includes taxes & fees
11 May - 12 May
Chambery Inn
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is SAR 1,594
SAR 1,749 total
includes taxes & fees
7 May - 8 May
Inn at Kenmore Hall
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (626)
"Friendly staffs. Home away from home. No elevators (the only inconvenience)!"
The price is SAR 402
SAR 501 total
includes taxes & fees
14 May - 15 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Gateways Inn & Restaurant
Room (King Room) | Iron/ironing board, free WiFi, bed sheets

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (186)
"Always a good place to stay. And so convenient to walk to all the restaurants and shops in town."
The price is SAR 693
SAR 809 total
includes taxes & fees
8 May - 9 May
Gateways Inn & Restaurant
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Standard Room | Premium bedding, pillowtop beds, in-room safe, desk

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (613)
"Staff was very nice and the room was clean and quiet. "
The price is SAR 465
SAR 520 total
includes taxes & fees
27 May - 28 May
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Clean, comfortable and quiet. Stay here frequently. Very friendly front desk. "
The price is SAR 409
SAR 457 total
includes taxes & fees
30 Apr - 1 May
The Black Swan Lee - Lenox, Ascend Hotel Collection
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
9.0 out of 10, Wonderful, (710)
"Manager (owner?) was friendly and helpful. Room was clean and spacious (had corner room). Very good for price. Some annoying ticking sound maybe from room heater throughout the night but otherwise no issues at all. Would stay here again."
The price is SAR 249
SAR 279 total
includes taxes & fees
30 Apr - 1 May
Monument Mountain Motel
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (85)
"Here’s the review translated into English: ⭐⭐⭐⭐⭐ (5 stars – if there were 8, we’d give 8!) We had an unforgettable stay at the Maple Farm Hotel! The accommodation is decorated with incredible attention to detail and taste – the warm wood, stylish furniture, and countless charming little touches create a beautiful, natural atmosphere. In the mornings, we were awakened by the cheerful chirping of birds, which was simply magical. We especially loved the cozy hours by the fireplace and the...
The price is SAR 559
SAR 604 total
includes taxes & fees
1 May - 2 May
Inn at Silver Maple Farm
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1004)
"Very clean well kept, comfortable stay. Had family business to tend to and was able to really relax and unwind."
The price is SAR 379
SAR 424 total
includes taxes & fees
18 May - 19 May
Quality Inn
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Free WiFi, bed sheets

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (442)
"Receptionist was excellent. The room had the smell of an old building so we opened the windows to air it out and then it was fine. A night stand was damaged so we informed the receptionist but overall we were comfortable. "
The price is SAR 285
SAR 318 total
includes taxes & fees
1 May - 2 May
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Wilder House Berkshires
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (21)
"Bert was great - he really tried to help after the Expedia website (and app) made it impossible for me to cancel my trip (my wife and I came down with Influenza A). There was little he could do as I had booked through Expedia. I ended up paying full price and am finding it impossible to communicate with Expedia..."
The price is SAR 574
SAR 641 total
includes taxes & fees
6 May - 7 May
Wilder House Berkshires
Quality Inn
Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1004)
"Room was clean and the frig was updated to a larger size, which was nice. There is a bit of a danger with the bathtub. It has a high step in and out of the shower/ tub. Pillows were too soft. There was no neck support."
The price is SAR 284
SAR 317 total
includes taxes & fees
15 May - 16 May
Quality Inn
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.
Don't see what you're looking for?
See all available properties in Chesterwood
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

What's the area like around Chesterwood?

Chesterwood is located in a scenic area of South Lee known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, check out the 8 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay close to Chesterwood?

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is one of the top choices for your stay based on our traveler data, and this B&B offers free breakfast and free parking. It's located just a short 0.4 mi (0.6 km) from Chesterwood. Other good choices within a few miles include The Red Lion Inn and New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge.

How many hotels are there close to Chesterwood?

Expedia has 8 hotels and other accommodations within a mile from Chesterwood.

If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood.

Where can I learn more about changing or cancelling my trip in the area near Chesterwood?

For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.

What can I see and do near Chesterwood?

You'll want to browse the exhibits at Norman Rockwell Museum and Mission House. Naumkeag Museum, The Mount, and Berkshire Theatre Festival are monuments to see when you're exploring the area around Chesterwood. Be sure to get some family photos at Berkshire Botanical Garden, Hoffman's Pottery, and Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.