Search Hotels with Pool in Stockbridge

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotels with Pool

Tonight
29 Sep - 30 Sep
Tomorrow
30 Sep - 1 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Top Stockbridge Hotels with Pool

Berkshire Mountain Lodge
Indoor pool

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (663)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
The price is 2.842.349 ₫
3.764.746 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Berkshire Mountain Lodge
Huttopia Berkshires
Outdoor pool

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is 2.587.494 ₫
2.890.231 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Huttopia Berkshires
The Springs Motel
Seasonal outdoor pool

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (68)
"Quiet and quaint place. I have stayed a couple of times."
The price is 2.705.384 ₫
2.967.807 ₫ total
includes taxes & fees
30 Sept - 1 Oct
The Springs Motel
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1009)
"great place have stayed several times, and hope to return."
The price is 4.726.137 ₫
6.458.702 ₫ total
includes taxes & fees
30 Oct - 31 Oct
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is 8.170.936 ₫
9.884.701 ₫ total
includes taxes & fees
14 Oct - 15 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Blackberry River Inn
Seasonal outdoor pool

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (136)
"Loved everything especially Lucas and Joe💟☮️"
The price is 4.339.333 ₫
4.990.233 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Blackberry River Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (803)
"Great place to stay for overnight stays. Breakfast was appreciated."
The price is 2.085.837 ₫
2.329.801 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Howard Johnson by Wyndham Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Meeting facility

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (883)
"Our stay was very pleasant "
The price is 2.590.134 ₫
2.893.180 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2027)
"Really nice place at a reasonable price"
The price is 2.616.242 ₫
3.211.983 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Vacation Village in the Berkshires
Element Lenox Berkshires
Indoor pool

Element Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
The price is 4.699.734 ₫
5.249.603 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Element Lenox Berkshires
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.
View all properties

Top Stockbridge Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What is there to see and do in Stockbridge?
Make a point to visit attractions such as Naumkeag Museum and Berkshire Botanical Garden. During your stay, visit sights such as National Shrine of the Divine Mercy, Norman Rockwell Museum and Housatonic River. The bars and historic landmarks are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Stockbridge?
Taking the local weather in Stockbridge into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.