Hotels near Chesterwood

Name: Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price range: $192 total

Search over 755 hotels from $192

Jul 26 - Jul 27

Tonight

Jul 27 - Jul 28

Tomorrow night

Featured Hotels near Chesterwood

0.26 mi from Chesterwood

Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

0.4 mi from Chesterwood

$472 nightly

$527 total

Aug 4 - Aug 5

Total includes taxes and fees

Guests of The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood enjoy access to free WiFi in public areas, conference space, and a seasonal outdoor pool. Free parking is included with your stay. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this luxury bed & breakfast include coffee/tea in a common area, a computer station, and a library.

Pool

Breakfast included

Tranquil 3 BR Stockbridge House w/ Private Deck!

0.85 mi from Chesterwood

At this vacation home, guests have access to features like laundry facilities.

Kitchen

Washer

0.85 mi from Chesterwood

At this cottage, guests have access to free WiFi in public areas. If you drive, take advantage of free parking.

Kitchen

Pet friendly

Secluded Family Home in Serene Stockbridge Woods

1.11 mi from Chesterwood

Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions

1.45 mi from Chesterwood

Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

1.62 mi from Chesterwood

$269 nightly

$269 total

Jul 27 - Jul 28

Total includes taxes and fees

Tanglewood Suites features a steam room and a garden. You can take advantage of free parking if you drive. Additional amenities include a picnic area and barbecue grills.

Breakfast included

Parking included

Free Cancellation

Reserve now, pay when you stay

2.06 mi from Chesterwood

$229 nightly

$256 total

Aug 13 - Aug 14

Total includes taxes and fees

Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.

Pool

Spa

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

Free Cancellation

4.09 mi from Chesterwood

$172 nightly

$192 total

Jul 30 - Jul 31

Total includes taxes and fees

Guests staying at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG enjoy features like 2 indoor pools, 2 outdoor pools, and a business center. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this family-friendly hotel include a seasonal outdoor pool, an arcade/game room, and express check-out.

Pool

Air conditioning

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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.

Chesterwood Hotels

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Great selection of hotels in Chesterwood

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Chesterwood hotels essential information

Accommodation	755 hotels
Lowest Price	$192
Highest Price	$527
Popular hotels	The Red Lion Inn, Classic Stockbridge Cottage, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Tranquil 3 BR Stockbridge House w/ Private Deck!, Tranquil 3 BR Stockbridge House w/ Private Deck!, Secluded Family Home in Serene Stockbridge Woods, Tanglewood Suites, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions

Recent Reviews

5/5 Excellent

"Miranda at the front desk was beyond accommodating. My mom and I enjoyed our stay in this historic hotel!"

A verified traveler stayed at The Red Lion Inn

Posted 4 days ago

5/5 Excellent

Great house for family - near Tanglewood

"We stayed here with my parents and toddler son and it was great. The house was really wonderful, has everything you could possibly need in it. The location is amazing, on a large forested area with easy walking paths. The owners were super responsive and came to fix an issue when it popped up immediately. "

A verified traveler stayed at Tranquil 3 BR Stockbridge House w/ Private Deck!

Posted 13 days ago

5/5 Excellent

"The house is just about perfect! We were able to get in quickly and many of the lights are intuitive - in logical places - so even though we didn't arrive till dusk, all was easy getting in.As we wandered and learned more about the house, we all marveled at the comfort. Chairs are comfortable, tables set in logical, easy reach, kitchen easily learnable. We enjoyed the art and the lack of sterility.We also enjoyed the nesting birds above the kitchen door. Mama was pretty cranky whenever we were in the dining area but I like to think that she got used to us and realized that we were all enchanted watching her come and go and feed her babies. We even saw one of them fledge! The second one was a bit later and we missed that one leaving but later that day, it was clear that the nest was empty. Thank you for the note on the door!I have two suggestions (?). One is that the master bedroom toilet has a loose rubber gasket which means that the toilet leaks slowly. Not a huge deal but pretty easily fixable, I believe.The other is that it might be a thought to put tall stakes as markers at the two large rocks on either side of the top of the driveway. By the time we left, we had them pretty much scoped out but still felt compelled to have someone outside the car to guide the driver. A couple of those thin orange rods might work well. We had three people in our party who have bum knees and so chose to use the upper entrance. Many thanks!!"

A verified traveler stayed at Classic Stockbridge Cottage

Posted 2 months ago

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Hotels near Chesterwood

Search over 755 hotels from $192

Featured Hotels near Chesterwood

Classic Stockbridge Cottage

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Tranquil 3 BR Stockbridge House w/ Private Deck!

Tranquil 3 BR Stockbridge House w/ Private Deck!

Secluded Family Home in Serene Stockbridge Woods

Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions

Tanglewood Suites

The Red Lion Inn

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

Chesterwood Hotels

Great selection of hotels in Chesterwood

Chesterwood hotel reviews, photos and virtual tours

Grab Chesterwood hotel deals and special offers

24/7 support with Chesterwood hotel reservations

Forget Orbitz change or cancel fees on Chesterwood hotels

Chesterwood hotels essential information

Recent Reviews

The Red Lion Inn

Tranquil 3 BR Stockbridge House w/ Private Deck!

Classic Stockbridge Cottage

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