The 10 best holiday rentals in Stockbridge, USA | Booking.com
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Holiday Rentals in Stockbridge

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The best holiday rentals in Stockbridge

Check out our pick of great 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
Check availability

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, 54 reviews
Price from
US$269
1 night, 2 adults
Check availability

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.

G
Gayle
From
United States
Perfection with meticulous care and service - attention to detail is unheard of at an Inn since 2020! With other places feeling worn and showing age with overuse- Granville owners continue to deliver exceptional quality and sophistication as hosts!
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 131 reviews
Price from
US$200
1 night, 2 adults
Check availability

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...

B
Beth
From
United States
We loved the kindness message and the staff was wonderful! Food was great and highly recommend taking a walk in Kennedy Park.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 555 reviews
Price from
US$153.51
1 night, 2 adults
Check availability

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$133
1 night, 2 adults
Check availability

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
Check availability

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
Check availability

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.

M
Matthew
From
United Kingdom
We loved how the host held on for us to arrive late (gone 10pm on Sunday!) Without him doing so we would of been totally screwed. We loved the great welcome we got from Ron even though we were later than expected, the atmosphere, the decor and location to town oh and the comfy bed.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 496 reviews
Price from
US$177
1 night, 2 adults
Check availability

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.

J
James
From
Canada
The building was from a different time. We loved it. The hospitality was terrific. The breakfasts were great.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 142 reviews
Price from
US$243
1 night, 2 adults
Check availability

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 8.4
Very good - What previous guests thought, 18 reviews
Price from
US$208.95
1 night, 2 adults
Check availability
All holiday rentals in Stockbridge

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

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Holiday Rentals with swimming pools in Stockbridge and nearby

  • Brook Farm Inn

    Lenox
    Swimming pool
    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$310.19 per night
  • 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

  • Devonfield Inn

    Lee
    Swimming pool
    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$445.68 per night

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

  • Chambery Inn

    Lee
    Free cancellation options available
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 34 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

  • The Constance by The Lenox Collection

    Lenox
    Free cancellation options available
    Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 496 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$194.36 per night

  • Gateways Inn

    Lenox
    Free cancellation options available
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 18 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$280.55 per night

  • The Cornell Inn, Lenox & The Berkshires

    Lenox
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 555 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
  • 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...

  • The Gatehouse on Golden Hill

    Lee
    Free cancellation options available

    Located in Lee, 7.5 km from Tanglewood Musical Center and 7.6 km from Tanglewood, The Gatehouse on Golden Hill offers air conditioning.

    From US$919.08 per night

  • Shaker Mill Inn

    West Stockbridge
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 87 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$159.73 per night
  • 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.

Enjoy breakfast in Stockbridge and nearby

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 131 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.

  • Eastgate Inn B&B

    Lenox
    Breakfast options
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 20 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.

  • 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
    Breakfast options
    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$212.23 per night
  • Scored out of 10, guest rating 7.1
    Good - What previous guests thought, 72 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.

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