Find Hotels with a Pool in South Lee, MA

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on South Lee Hotels with a Pool

This weekend
Next weekend

Top South Lee Hotels with a Pool

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

3.5 star property
South Lee
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (789)
Swimming enthusiasts rejoice at this four-pool paradise nestled in the Berkshires. Families appreciate the well-maintained waters complemented by sun loungers, umbrellas, and refreshing poolside drinks, creating memorable mountain getaways year-round.
The price is ₩156,659
₩195,523 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

4.5 star property
Stockbridge
  • Pool loungers
9.2 out of 10, Wonderful, (110)
Seasonal swimming awaits at this luxury bed & breakfast, where summer days unfold between pool loungers and excellent breakfasts. Adventure seekers can enjoy kayaking, mountain biking, and horseback riding before returning to individually furnished rooms.
The price is ₩561,797
₩679,614 total
includes taxes & fees
Dec 8 - Dec 9
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
  • Pool loungers
9.6 out of 10, Exceptional, (14)
Mountain adventures begin at the outdoor pool, complete with sun loungers and umbrellas for post-hike relaxation. Sauna sessions, complimentary bicycles, and nearby hiking trails complement the experience at this scenic Berkshire retreat.
The price is ₩382,455
₩476,495 total
includes taxes & fees
Nov 30 - Dec 1
Prospect Berkshires

Brook Farm Inn

3.5 star property
Lenox
  • Outdoor pool
  • Poolside bar
9.4 out of 10, Exceptional, (162)
Poolside cocktails enhance summer swims at this tranquil Berkshires retreat. Guests savor exceptional made-to-order breakfasts before relaxing in spacious, fireplace-equipped rooms. Nearby Tanglewood and hiking trails complete perfect seasonal getaways.
Brook Farm Inn

The Old Inn On The Green

4.0 star property
Great Barrington
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
9.2 out of 10, Wonderful, (90)
Refreshing waters beckon from the seasonal outdoor pool, open May through August amid lush garden grounds. After swimming, guests savor fantastic meals at the acclaimed on-site American restaurant, which offers breakfast, lunch, and dinner in an upscale setting.
The price is ₩448,649
₩541,394 total
includes taxes & fees
Nov 25 - Nov 26
The Old Inn On The Green

Sunset Inn

2.0 star property
Lee
  • Near the beach
7.6 out of 10, Good, (410)
Mountain recreation surrounds this quiet getaway featuring a refreshing seasonal pool open from August. After swimming, guests appreciate clean, comfortable rooms with mini fridges before exploring nearby skiing and hiking trails.
The price is ₩132,388
₩147,878 total
includes taxes & fees
Dec 2 - Dec 3
Sunset Inn

Blackberry River Inn

3.0 star property
Norfolk
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Business services
  • Housekeeping
9.4 out of 10, Exceptional, (159)
Dive into summer bliss at the seasonal outdoor pool, open June through September, after enjoying the complimentary cooked-to-order breakfast. Surrounded by quiet countryside, this bed & breakfast offers fireplace warmth, picnic areas, and attentive service from helpful staff.
The price is ₩241,756
₩278,019 total
includes taxes & fees
Nov 25 - Nov 26
Blackberry River Inn

Berkshire Inn

2.0 star property
Pittsfield
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
7.8 out of 10, Good, (838)
Seasonal outdoor pool beckons sun-seekers from June through August at this spotless, centrally located motel. After a day of skiing or downtown exploration, guests appreciate comfortable beds, updated rooms with refrigerators, and friendly service.
The price is ₩126,490
₩141,289 total
includes taxes & fees
Nov 25 - Nov 26
Berkshire Inn

Jiminy Peak Mountain Resort

3.0 star property
Hancock
  • Outdoor pool
  • Pool loungers
  • 2 hot tubs
8.2 out of 10, Very Good, (986)
Splash into alpine relaxation at the sun-drenched outdoor pool complete with loungers and umbrellas after a day on the slopes. Beyond swimming, this resort offers tennis courts, hiking trails, and a fitness center for complete mountain enjoyment.
The price is ₩219,176
₩244,819 total
includes taxes & fees
Nov 25 - Nov 26
Jiminy Peak Mountain Resort

Devonfield Inn B&B

4.0 star property
Lee
  • Outdoor pool
  • Pool loungers
10.0 out of 10, Exceptional, (133)
Surrounded by loungers for sun-soaked relaxation, the serene outdoor pool creates a perfect countryside escape. Guests savor complimentary gourmet breakfasts before exploring nearby hiking trails or enjoying a therapeutic massage at this charming B&B.
Devonfield Inn B&B
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.

Top South Lee Hotel Reviews

Frequently asked questions

What's it like visiting South Lee?
If lounging by a pool is your idea of the perfect getaway, you may want to consider luxurious South Lee, which has 9 places to stay with pools. During your visit, you can explore sights such as Housatonic River and National Shrine of the Divine Mercy, and then relax and unwind poolside at one of the accommodations in South Lee that guests like for their pools.
What are some accommodations with pools in South Lee?
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Vacation Village in the Berkshires: Offers a sauna, a communal pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool, and free self parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Offers a health club, an indoor pool, and complimentary wired internet access.
How many pool hotels will I be able to find in South Lee?
Expedia has 9 hotels in South Lee for your poolside break.
What is there to see and do in South Lee?
The picturesque setting of Housatonic River showcases the area's natural beauty. Discover sights such as Chesterwood during your stay. You'll also discover lost of options for restaurants and cheese shops in South Lee.
When is the best time to book a hotel with a pool in South Lee?
Taking into account the local weather in South Lee can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in South Lee are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.