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Our top choices for Chesterwood hotels

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.

1. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
5.3 mi from Chesterwood
United States
Bob
$119 nightly
$133 total
Nov 2 - Nov 3
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A café with a display case, a frozen food section, and a marketplace sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

2. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
4.2 mi from Chesterwood
United States
Jared
$135 nightly
$150 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

3. The Yankee Inn

The Yankee Inn
9.3 mi from Chesterwood
United States
Basil
$106 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A hotel room with a bed, a desk, a television, a microwave, and a sofa.
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

4. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
5.7 mi from Chesterwood
United States
Christine
$93 nightly
$103 total
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Lee - Lenox South
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

5. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
9.6 mi from Chesterwood
United States
James
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A calm lake at dusk with a wooden dock and two chairs facing the water.
A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.
A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.
A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

6. Berkshire Lake Lodge

Berkshire Lake Lodge
10 mi from Chesterwood
United States
mike
$126 nightly
$141 total
Nov 5 - Nov 6
Total with taxes and fees
Berkshire Lake Lodge
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A covered outdoor area with stone pillars and a view of a road and green hills.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

7. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
7.5 mi from Chesterwood
United States
Tracy
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
9.9 mi from Chesterwood
United States
marilyn
$115 nightly
$128 total
Nov 8 - Nov 9
Total with taxes and fees
Berkshire Mountain Lodge
A red building with a sign reading "Shaker Mill Inn."
A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

9. Shaker Mill Inn

Shaker Mill Inn
3.6 mi from Chesterwood
United States
Steven
$132 nightly
$145 total
Nov 9 - Nov 10
Total with taxes and fees
Shaker Mill Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern cafe with a counter, seating area, and large windows.
A snack bar with shelves of snacks and a refrigerated display.

10. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
9.6 mi from Chesterwood
United States
Sheldon
$99 nightly
$111 total
Nov 9 - Nov 10
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

11. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
7.8 mi from Chesterwood
United States
Kirsty
$143 nightly
$160 total
Nov 8 - Nov 9
Total with taxes and fees
Element by Marriott Lenox Berkshires
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Living area
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

12. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
9.1 mi from Chesterwood
United States
Thomas
$114 nightly
$127 total
Nov 7 - Nov 8
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A large house with a balcony and a grassy yard.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.
A two-story building with a gabled roof and a chimney.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

13. The Little Lion

The Little Lion
3.2 mi from Chesterwood
United States
Lidia
$115 nightly
$128 total
Oct 18 - Oct 19
Total with taxes and fees
The Little Lion
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

14. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
10.5 mi from Chesterwood
United States
Joe
$93 nightly
$104 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

15. East Rock Inn

East Rock Inn
6.3 mi from Chesterwood
United States
ERIK
$125 nightly
$140 total
Nov 8 - Nov 9
Total with taxes and fees
East Rock Inn
Front of property
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
Exterior
A stone fountain surrounded by trees in a park setting.

16. The Inn at Stockbridge

The Inn at Stockbridge
3.2 mi from Chesterwood
United States
Jodi
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

17. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
9.3 mi from Chesterwood
United States
Mark
$79 nightly
$88 total
Oct 18 - Oct 19
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A two-story building with a sign reading "Chambéry Inn".
A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.
A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.
A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

18. Chambery Inn

Chambery Inn
5.4 mi from Chesterwood
United States
Alexandra
$294 nightly
$328 total
Nov 8 - Nov 9
Total with taxes and fees
Chambery Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A modern apartment with a living room, kitchenette, and dining area.

19. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
12.2 mi from Chesterwood
United States
Rena
$89 nightly
$100 total
Nov 1 - Nov 2
Total with taxes and fees
The Central Downtown Inn & Suites
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
A cozy library with bookshelves, a fireplace, and comfortable seating.

20. Berkshires Untold

Berkshires Untold
8.1 mi from Chesterwood
United States
Madhavi R
$136 nightly
$152 total
Nov 1 - Nov 2
Total with taxes and fees
Berkshires Untold
View all properties

Compare popular hotels close to Chesterwood

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
9.2
Wonderful
1,001 reviews
View
A building with a porch and multiple windows, surrounded by purple flowers.
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
9.2
Wonderful
1,003 reviews
View
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
The Yankee Inn
9.2
Wonderful
1,000 reviews
View
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
Quality Inn Lee - Lenox South
8.6
Excellent
1,000 reviews
View
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
Hilton Garden Inn Lenox Pittsfield
9.2
Wonderful
712 reviews
View

Hotels recommended for families near Chesterwood

A large house with a balcony and a grassy yard.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.
A two-story building with a gabled roof and a chimney.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

The Little Lion

The Little Lion
Great Barrington
$115 nightly
$128 total
Oct 18 - Oct 19
Total with taxes and fees
The Little Lion
Front of property
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
Exterior
A stone fountain surrounded by trees in a park setting.

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A café with a display case, a frozen food section, and a marketplace sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
$135 nightly
$150 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.
A porch with a wooden table and two wicker chairs, a small stool, and a window with blinds.
A dining area with a wooden table, black chairs, and a vase with green plants.
A kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, and a window with a view of trees.

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
$314 nightly
$351 total
Oct 13 - Oct 14
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern hotel lobby with seating areas, tables, and a reception desk.
A breakfast area with a counter, coffee machine, and a display of pastries.
A kitchenette with a microwave, coffee maker, and coffee cups.
A hotel room with two beds, a desk, a TV, and a window with curtains.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
$93 nightly
$104 total
Nov 9 - Nov 10
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
$119 nightly
$133 total
Nov 2 - Nov 3
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.
A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.
A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
$79 nightly
$88 total
Oct 18 - Oct 19
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A row of white plastic chairs on a covered outdoor area with a white building in the background.
A motel with a parking lot and several cars parked.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

Monument Mountain Motel

Monument Mountain Motel
Great Barrington
$67 nightly
$74 total
Nov 1 - Nov 2
Total with taxes and fees
Monument Mountain Motel

Top Chesterwood Hotel Reviews

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

10/10 Excellent
"We found the Taggart House to be so convenient to the town of Stockbridge - it was a pleasure to be able to walk to the park with our kids, pick up a delicious local coffee or simply do some shopping in the interesting local shops. Even though it was close and on main street, it is set on the back part of the property overlooking the Housitonic River which was lovely, relaxing, very quiet and peaceful. We enjoyed the spaciousness of the home and the large kitchen, the rain showers in all of the bathrooms, two oversized soaking tubs and it was a real treat to have a laundry room on both floors! A big Thank You! to the owners for sharing their home for our family vacation!"
Sandy M. 8-night trip
Posted 13 hours ago
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 2 days ago
The Red Lion Inn
Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay

Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay

10/10 Excellent
"The home was exactly as expected - So beautiful and accommodating. Communication with the host was excellent. We had a wonderful time in Woodland Zen. Can’t wait to return!"
gary t. 28-night trip
Posted 5 days ago
Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent
"The house is gorgeous and so cozy. Beautiful views of all the trees, secluded and quiet. It was perfect for our stay. Tom was very accommodating and communicative, it was such a delight I’ll never forget our stay here."
Ellen M. 3-night trip
Posted 10 days ago
Secluded Family Home in Serene Stockbridge Woods
3-bedroom duplex in Stockbridge on the river

3-bedroom duplex in Stockbridge on the river

10/10 Excellent
"This is an absolutely beautiful spot. We did not stay long enough. Very clean and spacious. Beautiful river side yard. Tons of things to do in the cute nearby towns. Loved our stay and would recommend to others."
Jennie O. 2-night trip
Posted 12 days ago
3-bedroom duplex in Stockbridge on the river
Classic Stockbridge Cottage

Classic Stockbridge Cottage

10/10 Excellent
"We thoroughly enjoyed our stay at this property. It was comfortable, clean and exactly liked the photos showed.Would definitely stay again."
Marjoroe D. 3-night trip
Posted 2 weeks ago
Classic Stockbridge Cottage
Spacious Retreat Near Tanglewood & Ski Resorts

Spacious Retreat Near Tanglewood & Ski Resorts

10/10 Excellent
"The house was excellent and had everything you could need plus! Very clean, many bedrooms. Kitchen well stocked with cooking utensils etc. large yards front and back which were great for yard games. The host was very responsive and helpful. Would definitely stay here again."
Robert D. 2-night trip
Posted 3 weeks ago
Spacious Retreat Near Tanglewood & Ski Resorts
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

10/10 Excellent
"The Taggart House exceeded our expectations. We were a group 5 women, grade school BFFs, celebrating a milestone birthday….. loved having our own bedrooms and bathrooms, more so because they were totally renovated. The sun porch was our favorite spot for everything - cozy, comfy and gorgeous. Our hosts happened to be nearby over the weekend and even set up our evening fire pit to ensure the required s’more-fest was a success. Highly recommend!"
Margaret P. 4-night trip
Posted 1 month ago
A Grand property in Historic Stockbridge
Hearth House | Prime Location!

Hearth House | Prime Location!

10/10 Excellent
"Comfortable home in a great neighborhood."
lauren S. 3-night trip
Posted 1 month ago
Hearth House | Prime Location!

Other attractions near Chesterwood

Norman Rockwell Museum

9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
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Berkshire Botanical Garden

9.4/10 (14 reviews)
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
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Mission House

9.6/10 (5 reviews)
You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area.
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Naumkeag Museum

9.4/10 (10 reviews)
You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.
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National Shrine of the Divine Mercy

9.0/10 (83 reviews)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
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Schantz Galleries

7.2/10 (5 reviews)
You can spend an afternoon exploring the galleries in Schantz Galleries during your trip to Stockbridge. Wander the lakeside in this quaint area.
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Art et Industrie

8.0/10 (5 reviews)
You can spend an afternoon exploring the galleries in Art et Industrie in Great Barrington. Amble around this quaint area's gardens, or seek out the hiking trails.
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Berkshire Theatre Festival

8.8/10 (3 reviews)
You can get tickets for a performance at Berkshire Theatre Festival on your trip to Stockbridge. Wander the lakeside in this quaint area.
See properties

Frequently asked questions

What are the top-rated hotels near Chesterwood?
Discover the top-rated hotels near Chesterwood in South Lee that provide exceptional stays and stunning views for travelers seeking a memorable experience.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse offers a luxurious escape with breathtaking river views, just 2.0 miles from Chesterwood. Rated an impressive 10 by travelers, this modern retreat accommodates up to 10 travelers, perfect for larger groups. Guests can enjoy amenities such as a fully equipped kitchen with a dishwasher, oven, and coffee maker, along with a spacious patio and garden area for relaxation.Vacation in a Berkshire FarmhouseLocated 2.9 miles from Chesterwood, the Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8. This historic hotel combines charm with modern comforts, featuring a well-equipped kitchen, outdoor play areas, and nearby hiking trails. Guests can unwind on the patio or explore local attractions such as wineries and ski resorts, making it a versatile choice for all travelers.The Inn at StockbridgeThe Inn at Stockbridge is a 4-star gem just 4.1 miles from Chesterwood, rated 9.8 by travelers. Guests can indulge in complimentary cooked breakfasts and relax by the outdoor pool. With a variety of amenities, including a spa, fitness facilities, and beautifully designed rooms with premium bedding, this inn perfectly blends comfort and elegance, creating a peaceful retreat amidst the stunning Berkshire landscape.
What hotels are within walking distance to Chesterwood?
Discover cozy accommodations just a short stroll from Chesterwood, perfect for travelers seeking top-rated stays!The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodThe Stockbridge Country Inn is a charming 4.5-star bed and breakfast located just a 12-minute walk from Chesterwood, with an excellent review rating of 9.2. Guests can enjoy delightful amenities such as complimentary breakfast options, an onsite art gallery, and a terrace for relaxation. Outdoor enthusiasts will appreciate the hiking and biking trails nearby, along with a golf course located just a short distance away. The inn boasts a luxurious historic design, complete with premium bedding and a fireplace, ensuring a comfortable and memorable stay.
How much is a hotel near Chesterwood?
Staying near Chesterwood is a treat, with plenty of hotels from $88 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a vacation during weekends or around public holidays.
What are the most popular family-friendly hotels near Chesterwood?
For families seeking a delightful stay near Chesterwood, these top-rated hotels offer family-friendly amenities ensuring a memorable getaway.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse: Modern Luxury Meets Nature is only 2.0 miles from Chesterwood and enjoys a perfect 10 travelers' rating. This unique hotel offers a cozy kitchen and a lovely patio, perfect for family gatherings. With a travel crib and stair gate for children, it ensures safety and comfort for younger travelers. The stunning river views and nearby nature trails make it an ideal retreat for families looking to connect and unwind.Vacation in a Berkshire FarmhouseVacation in a Berkshire Farmhouse is a fantastic option just 2.9 miles from Chesterwood, an impressive travelers' rating of 9.8. This inviting farmhouse features amenities tailored for families, including a spacious kitchen, outdoor play area for children, and a variety of toys to keep the little ones entertained. With a beautiful garden and patio, parents can relax while kids explore. Guests also enjoy nearby hiking, skiing, and antique shopping.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGHoliday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG, located 4.7 miles from Chesterwood, offers a family-friendly environment with a review rating of 9.0 and a 3.5-star rating. Families will appreciate the onsite playground, arcade game room, and spacious rooms equipped with kitchen facilities and a crib at no extra charge. Guests can also take advantage of the indoor and outdoor pools, hot tub, and nearby skiing activities for a fun-filled family vacation.
Which hotels near Chesterwood offer the best views?
For travelers seeking top-rated hotels with stunning views near Chesterwood, South Lee offers some delightful options.Vacation in a Berkshire FarmhouseLocated just 2.9 miles from Chesterwood, this charming farmhouse is rated an impressive 9.8 by travelers. Guests can relish breathtaking mountain views from the patio and enjoy outdoor adventures, including hiking and skiing nearby. The hotel features a fully equipped kitchen, a cozy garden, and ample parking, making it a perfect retreat for nature lovers who appreciate rustic charm.The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodJust a short 12-minute walk from Chesterwood, this 4.5-star inn is rated 9.2 by travelers. Guests are treated to scenic mountain views from the terrace and can indulge in complimentary full breakfasts. With amenities like a pool, hiking options on-site, and a charming historic design, this inn provides a cozy and luxurious feel, making it an ideal spot for art and nature enthusiasts alike.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGThis 3.5-star resort is situated 4.7 miles from Chesterwood and boasts a review rating of 9.0. Guests can take advantage of the outdoor and indoor pools, hot tubs, and on-site tennis courts. The resort's balconies and patios offer lovely resort views, perfect for relaxation after a day of exploring. With family-friendly amenities and a variety of activities, it's a delightful choice for those looking to enjoy the Berkshires.
What are the best affordable hotels near Chesterwood?
For travelers seeking top-rated yet affordable hotels near Chesterwood, these charming properties offer the perfect blend of comfort and convenience without breaking the bank.Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10Taggart Treehouse is a spacious retreat just 2.0 miles from Chesterwood, rated an impressive 10 by travelers. This hotel features stunning river views and is perfect for families or groups, providing amenities like a fully equipped kitchen with a dishwasher and an oven, plus a cozy patio to enjoy the outdoors. Guests can also benefit from onsite parking and WiFi, ensuring a comfortable stay.Vacation in a Berkshire FarmhouseJust 2.9 miles from Chesterwood, Vacation in a Berkshire Farmhouse boasts a remarkable review rating of 9.8. This family-friendly farmhouse features an outdoor play area for children and is surrounded by opportunities for hiking, skiing, and winery tours. Guests can enjoy a kitchen equipped with modern appliances, a charming patio, and WiFi to stay connected during their stay.Shaker Mill InnLocated 4.9 miles from Chesterwood, Shaker Mill Inn is a cozy escape with a review rating of 9.6. This inn offers a free breakfast and self-parking, making it a convenient choice for travelers. Guests can relax in their rooms featuring a kitchenette and enjoy the beautiful garden or the private hot tub. With contactless check-in and a warm atmosphere, it's a delightful option for a restful stay.
Are there any hotels with pools close to Chesterwood?
For those seeking a refreshing stay near Chesterwood, these top-rated hotels with pools offer the perfect retreat for relaxation and fun.The Inn at StockbridgeThe Inn at Stockbridge, just 4.1 miles from Chesterwood, is a sophisticated 4-star retreat with an outstanding review rating of 9.8. This hotel features a serene outdoor pool surrounded by beautiful gardens, ideal for relaxation. Guests are treated to complimentary breakfast and access to a 24-hour fitness center, ensuring a comfortable and energizing stay.The Red Lion InnLocated only 2.3 miles from Chesterwood, The Red Lion Inn boasts a charming 3.5-star experience with a review rating of 8.8. Guests can unwind in the outdoor pool area, featuring comfortable sun loungers. This historic hotel offers a variety of amenities including a spa, 24-hour room service, and easy access to skiing and snowboarding activities, perfect for those looking to explore the nearby mountains.Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHGSituated just 4.7 miles from Chesterwood, the Holiday Inn Club Vacations Oak n' Spruce Resort is a family-friendly gem with an impressive review rating of 9.0. Guests can enjoy both indoor and outdoor pools, complete with sun loungers and a poolside bar for leisurely afternoons. Additional highlights include a hot tub, mini-golf, and on-site tennis facilities, making it an ideal choice for families and outdoor enthusiasts alike.
What are the best pet-friendly hotels near Chesterwood?
For travelers with pets visiting Chesterwood, finding a welcoming and comfortable hotel is a breeze with these top-rated options nearby.Vacation in a Berkshire FarmhouseJust 2.9 miles from Chesterwood, Vacation in a Berkshire Farmhouse is an idyllic retreat for pet owners, allowing pets in-room. With an outstanding review rating of 9.8, this farmhouse boasts a historic charm and offers a plethora of amenities that include a kitchen, outdoor play area for children, and nearby hiking opportunities. Guests can unwind on the patio or explore local attractions, making it an excellent choice for families and travelers with pets alike.The Inn at StockbridgeThe Inn at Stockbridge, located 4.1 miles from Chesterwood, is a charming 4-star hotel that welcomes dogs only. With a remarkable review rating of 9.8, this inn features an outdoor pool, spa services, and a lovely garden area, perfect for relaxing with pets. Guests can indulge in a complimentary cooked breakfast and enjoy comfortable accommodations with premium bedding and designer toiletries, ensuring a delightful stay for both you and your furry friend.Econo Lodge Lee - Great BarringtonEcono Lodge Lee - Great Barrington is just 5.0 miles from Chesterwood and offers a cozy stay for travelers with pets. This budget-friendly hotel allows pets in-room, making it a great choice for those traveling with furry companions. Guests can enjoy amenities like daily housekeeping, free continental breakfast, and access to a mini-golf course on-site. Rated by travelers at 6.4, it's a convenient option for families looking to explore the beautiful Berkshire region.
Can I book a fully refundable hotel close to Chesterwood?
Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Chesterwood", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.

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