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Holiday Rentals in Stockbridge

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The best holiday rentals in Stockbridge

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Stockbridge Country Inn

Stockbridge

Featuring a garden and views of mountain, Stockbridge Country Inn is a bed and breakfast situated in a historic building in Stockbridge, 1.5 km from Norman Rockwell Museum.

L
Leslie
From
France
Very friendly owner and lovely country inn.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 14 reviews
Price from
US$309.47
1 night, 2 adults

The Cottage

Stockbridge

Situated in Stockbridge, 3.3 km from Norman Rockwell Museum, The Cottage has a private beach area, parking on-site and rooms with free WiFi access.

G
Gail
From
United Kingdom
Beautiful location and the owner was very welcoming and chatty. She also provided helpful advice on where to hike and where to eat, which was excellent given we only had one full day there. The bed was comfortable and the size of the unit was generous.
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 52 reviews
Price from
US$269
1 night, 2 adults

Granville House

Great Barrington (Near Stockbridge)

Situated within 10 km of Norman Rockwell Museum and 17 km of Tanglewood Musical Center, Granville House features rooms with air conditioning and a private bathroom in Great Barrington.

M
Miri
From
Israel
A house full of character, art and collections. A friendly host and a superb breakfast.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 134 reviews
Price from
US$200
1 night, 2 adults

The Cornell Inn, Lenox & The Berkshires

Lenox (Near Stockbridge)

Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee...

G
Gabrielle
From
Australia
Our welcome was amazing and friendly, bonus drink to settle in with, and great local knowledge. Breakfast was delicious, served in a beautifully ambient room, and our room was gorgeous, bed comfy.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 551 reviews
Price from
US$153.51
1 night, 2 adults

Shaker Mill Inn

West Stockbridge (Near Stockbridge)

Set within 6.3 km of Tanglewood Musical Center and 6.6 km of Tanglewood, Shaker Mill Inn offers rooms with air conditioning and a private bathroom in West Stockbridge.

R
Robert
From
Canada
Very spacious and comfortable suite. Warm welcome from John. Very nice breakfast provisions in the room Close to Tanglewood and convenient to other attractions in the Berkshires. Highly recommended.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 87 reviews
Price from
US$131
1 night, 2 adults

Devonfield Inn

Lee (Near Stockbridge)

Situated just 6.1 km from Cranwell Spa & Golf Club, Devonfield Inn features accommodation in Lee with access to a garden, a shared lounge, as well as a shared kitchen.

L
Lesley- Ann
From
South Africa
We had the most wonderful time at this beautiful inn set in stunning surroundings and gardens. On our holiday this was the only place where we actually met and interacted with the owners , Doug and Jim. Our room was comfortable, clean and had everything we needed. Lovely leather chairs and decor. The bed was comfortable with nice linens. We were invited to the cheese and wine evening and it was great. Lovely wines and cheeses and a great way to meet other guests. We so enjoyed the piano and a few songs from Doug. Breakfast was a feast .. fruit, yogurts , eggs . Delicious and a different menu each morning. Home baked cakes .. yummy. Saturday we sat in the gardens and enjoyed a lovely afternoon of music , it was so nice to see locals join the afternoon too. We wish we could have stayed longer.. Doug and Jim you run a beautiful Inn, your commitment and hard-work tells the story. Thank you!
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 15 reviews
Price from
US$369
1 night, 2 adults

Brook Farm Inn

Lenox (Near Stockbridge)

Situated within 3 km of Tanglewood and 3.1 km of Cranwell Spa & Golf Club, Brook Farm Inn features rooms with air conditioning and a private bathroom in Lenox.

V
Virginie
From
United States
Beautifully arranged. A lot of details and love were put into this b&b. The breakfast was simple but absolutely delicious and homemade. We loved every minute of it. We will go back in summer
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 45 reviews
Price from
US$208.10
1 night, 2 adults

The Constance by The Lenox Collection

Lenox (Near Stockbridge)

Set in Lenox, 2.4 km from Tanglewood Musical Center, The Constance by The Lenox Collection offers accommodation with a fitness centre, free private parking, a garden and a terrace.

C
Corinna
From
Germany
Beautiful hotel with lovely and very helpful staff
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 496 reviews
Price from
US$183
1 night, 2 adults

Whistler's Inn

Lenox (Near Stockbridge)

Boasting a garden and views of mountain, Whistler's Inn is a bed and breakfast set in a historic building in Lenox, 3 km from Tanglewood Musical Center.

C
Carol
From
France
The hosts were lovely and helpful. We had a wonderful stay,
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 140 reviews
Price from
US$243
1 night, 2 adults

Gateways Inn

Lenox (Near Stockbridge)

Located in Lenox and only 2.4 km from Cranwell Spa & Golf Club, Gateways Inn provides accommodation with quiet street views, free WiFi and free private parking.

C
Christopher
From
United Kingdom
Gateways was the perfect place for our stay. It's a beautiful old house in the heart of Lenox with friendly, caring staff who will ensure your stay is memorable. It exceeded expectations in every way.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 19 reviews
Price from
US$208.95
1 night, 2 adults
All holiday rentals in Stockbridge

Most booked holiday rentals in Stockbridge and surroundings in the past month

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Popular with guests booking holiday rentals in Stockbridge

Popular with guests booking holiday rentals in Stockbridge

Popular with guests booking holiday rentals in Stockbridge

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2 reviews

Popular with guests booking holiday rentals in Stockbridge

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 3 reviews

Popular with guests booking holiday rentals in Stockbridge

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Popular with guests booking holiday rentals in Stockbridge

Scored out of 10, guest rating 7.3
Good - What previous guests thought, 52 reviews

Popular with guests booking holiday rentals in Stockbridge

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking holiday rentals in Stockbridge

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 15 reviews

Popular with guests booking holiday rentals in Lenox

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 550 reviews

Popular with guests booking holiday rentals in Lenox

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 142 reviews

Highly rated holiday rentals in Stockbridge and nearby

Devonfield Inn

Lee
8.0+ review score
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 15 reviews

Situated just 6.1 km from Cranwell Spa & Golf Club, Devonfield Inn features accommodation in Lee with access to a garden, a shared lounge, as well as a shared kitchen.

From US$423.34 per night

Chambery Inn

Lee
8.0+ review score
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 33 reviews

This historic Massachusetts bed and breakfast boasts free Wi-Fi access. Cable TV and an en suite bathroom are featured in every uniquely styled room. Ski Butternut is 13 miles away.

From US$212.22 per night
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 85 reviews

Set within 6.3 km of Tanglewood Musical Center and 6.6 km of Tanglewood, Shaker Mill Inn offers rooms with air conditioning and a private bathroom in West Stockbridge.

From US$139.63 per night
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 133 reviews

Situated within 10 km of Norman Rockwell Museum and 17 km of Tanglewood Musical Center, Granville House features rooms with air conditioning and a private bathroom in Great Barrington.

From US$257.63 per night

Brook Farm Inn

Lenox
8.0+ review score
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 45 reviews

Situated within 3 km of Tanglewood and 3.1 km of Cranwell Spa & Golf Club, Brook Farm Inn features rooms with air conditioning and a private bathroom in Lenox.

From US$291.54 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 492 reviews

Set in Lenox, 2.4 km from Tanglewood Musical Center, The Constance by The Lenox Collection offers accommodation with a fitness centre, free private parking, a garden and a terrace.

From US$198.83 per night

Gateways Inn

Lenox
8.0+ review score
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 19 reviews

Located in Lenox and only 2.4 km from Cranwell Spa & Golf Club, Gateways Inn provides accommodation with quiet street views, free WiFi and free private parking.

From US$233.63 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 550 reviews

Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee...

From US$244.62 per night

Holiday Rentals with swimming pools in Stockbridge and nearby

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 1 review

Featuring air-conditioned accommodation with a private pool, Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing is set in Lee.

From US$916.11 per night

These holiday rentals in Stockbridge and nearby have options with free cancellation

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 3 reviews

Situated 10 km from Tanglewood Musical Center, 10 km from Tanglewood and 10 km from Norman Rockwell Museum, Cordelia by AvantStay Amazing Backyard 10mins from Stockbridge features accommodation set in...

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5 reviews

Offering lake views, Lakefront Berkshires Retreat with Deck, Dock and Boat! is an accommodation located in Great Barrington, 16 km from Tanglewood Musical Center and 16 km from Tanglewood.

Eastgate Inn B&B

Lenox
Free cancellation options available
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 22 reviews

Offering a garden and garden view, Eastgate Inn B&B is set in Lenox, 600 metres from Tanglewood Musical Center and 1 km from Tanglewood.

Walk to Dining Downtown Lenox Guest House!

Lenox
Free cancellation options available
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 8 reviews

Situated 2.5 km from Tanglewood Musical Center, 2.7 km from Tanglewood and 11 km from Norman Rockwell Museum, Walk to Dining Downtown Lenox Guest House! features accommodation located in Lenox.

Whistler's Inn

Lenox
Free cancellation options available
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 142 reviews

Boasting a garden and views of mountain, Whistler's Inn is a bed and breakfast set in a historic building in Lenox, 3 km from Tanglewood Musical Center.

From US$234.57 per night

The Dewey by The Lenox Collection

Lenox
Free cancellation options available
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 69 reviews

This bed and breakfast in the scenic Berkshires boasts uniquely styled guest rooms, each with a private bathroom. Hiking and bicycle trails in Kennedy Park are just 1 mile away.