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Search Hotels with Babysitting Services in Stockbridge

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Recommended hotels in Stockbridge

Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1004)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
The price is 3.946.050 ₫
5.583.134 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Suite, Private Bathroom (RedBird Suite) | View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is 10.047.169 ₫
12.154.218 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites

Tanglewood Suites

Tanglewood Suites
2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is 5.761.233 ₫
5.761.233 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Tanglewood Suites
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (12)
"New hotel very nice"
United States
joel
The price is 3.446.217 ₫
3.849.424 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Element Lenox Berkshires
Exterior
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is 6.629.364 ₫
8.286.546 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Prospect Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is 2.867.463 ₫
3.145.607 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Shaker Mill Inn
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.638.592 ₫
2.947.307 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is 1.855.959 ₫
2.073.105 ₫ total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is 2.009.194 ₫
2.244.270 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
United States
regina maria
The price is 2.814.849 ₫
3.144.186 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.
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Frequently asked questions

How much do hotels with childcare in Stockbridge cost?
Prepare to pay between 2.073.105 ₫ and 12.154.218 ₫ per night for hotels with childcare in Stockbridge. Whatever your budget, the perfect stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with childcare in Stockbridge?
Pick from multiple hotels with childcare in Stockbridge with a total average guest review rating of 8.8. Holiday Inn Club Holidays Oak 'n Spruce Resort is a popular choice if you want your youngsters looked after while you have a well-earned break. This 2-star stay also features a sauna and a tennis court. Seven Hills Inn is another recommended option with babysitting services. It has a 2-star rating and amenities including a swimming pool and childcare services.
How many hotels with childcare are there in Stockbridge?
Stockbridge has 1 hotels with childcare. Ready to find a getaway where you can take a breather while your kids are with the babysitter? Lock it in with Expedia in just a few clicks.
What are the best cheap hotels with childcare in Stockbridge?
Hotels with childcare start from 2.073.105 ₫ per night, so your Stockbridge getaway doesn't need to cost a fortune! Holiday Inn Club Holidays Oak 'n Spruce Resort is a wallet-friendly pick highly rated by parents. Take advantage of on-site babysitting services when you need some time out, on top of a tennis court and a sauna. Seven Hills Inn is another inexpensive stay with childcare. A swimming pool and childcare services help make it a sought-after choice for many travellers. If you're sightseeing in Stockbridge and want to save money, there are plenty of free attractions to add to your to-do list. Lake Mansfield Park and Furnace Brook Winery at Hilltop Orchards are always popular. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly hotels with childcare in Stockbridge?
Holiday Inn Club Holidays Oak 'n Spruce Resort makes travelling with the little ones super easy. Just drop them off at the on-site childcare and treat yourself to some precious "me" time. This family-friendly property in Stockbridge has a 2-star rating and amenities including a sauna and a laundry service. After checking in and kicking back together in your cosy new digs, it's time to discover the local sights. Pleasant Valley Wilderness Sanctuary and Berkshire Scenic Railway Museum are top family-friendly attractions in Stockbridge.
Why book your hotel with childcare in Stockbridge with Expedia?
Incredible prices, flexible travel policies and search filters that make it easy to find the ideal fit are among the reasons to book with Expedia. Plus, we know that holidaying with kiddos can be demanding! Choose one of our hotels with childcare in Stockbridge and you'll be able to leave them with somebody else while you get some relaxation time.
How can I find cheap hotels with childcare in Stockbridge?
Expedia can help you search for cheap hotels with childcare in Stockbridge. Scroll down to our "traveller experience" filter and select "family friendly." This will show you a list of properties that come with family essentials, such as babysitting services and activities for the kids. You can also pick your hotel star rating and budget to save money on your stay.
What is there to do in Stockbridge near my hotel with childcare?
You'll find plenty of fantastic things that'll fill up your itinerary in Stockbridge. Make tracks to big attractions like Norman Rockwell Museum, Berkshire Theatre Festival and Naumkeag Museum. Mission House, Schantz Galleries and National Shrine of the Divine Mercy are other must-see's.