Find Hotels with an Outdoor Pool in Lee, MA

Start date: Check-in selected.
To Date
End date: Check-out
  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Lee Hotels with an Outdoor Pool

This weekend
Next weekend

Top Lee Hotels with an Outdoor Pool

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (1007)
Shimmering waters beckon at dual pool options, where indoor relaxation meets seasonal outdoor splendor. After exploring nearby Bousquet Ski Area, guests unwind in the rejuvenating hot tub while mountain vistas provide a stunning backdrop for aquatic serenity.
$64 nightly
The price is $72
Dec 7 - Dec 8
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (825)
Sparkling waters beckon at the inviting outdoor pool, a refreshing retreat after exploring nearby Tanglewood Music Center. Deep soaking bathtubs and hydromassage showers in clean, spacious rooms complement this conveniently located getaway.
$79 nightly
The price is $88
Nov 25 - Nov 26
Total with taxes and fees
Howard Johnson by Wyndham Lenox

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.
$86 nightly
The price is $97
Dec 3 - Dec 4
Total with taxes and fees
Sunset Inn

The Red Lion Inn

3.5 star property
Stockbridge
  • Outdoor pool
  • Pool loungers
8.8 out of 10, Excellent, (1002)
Sparkling waters invite refreshment at the outdoor pool, complemented by a rejuvenating hot tub that remains open year-round. Beyond aquatic pleasures, this historic hotel enchants with excellent dining, tasteful accommodations, and friendly service.
$184 nightly
The price is $206
Dec 21 - Dec 22
Total with taxes and fees
The Red Lion Inn

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

3.5 star property
South Lee
  • 2 outdoor pools
  • 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.
$119 nightly
The price is $133
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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.
$81 nightly
The price is $91
Dec 1 - Dec 2
Total with taxes and fees
Berkshire Inn

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.
$149 nightly
The price is $166
Nov 25 - Nov 26
Total with taxes and fees
Brook Farm Inn

The Little Lion

3.0 star property
Great Barrington
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • Extra beds/cribs
8.6 out of 10, Excellent, (544)
Aquatic adventures beckon with access to a nearby outdoor pool, complementing garden strolls at this cozy Berkshire motel. Nestled close to Norman Rockwell Museum and Ski Butternut, guests praise the helpful staff and comfortable accommodations.
$128 nightly
The price is $144
Dec 14 - Dec 15
Total with taxes and fees
The Little Lion

The Ponds at Foxhollow

3.0 star property
Lenox
  • Outdoor pool
  • Pool loungers
  • Hot tub
8.6 out of 10, Excellent, (134)
Swimmers glide through crystal waters at indoor and outdoor pools surrounded by serene Berkshire landscapes. Beyond aquatic pleasures, this resort boasts tennis courts, a sauna, and spacious accommodations with cozy fireplaces and full kitchens.
$120 nightly
The price is $135
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow

The Inn at Stockbridge

4.0 star property
Lee
  • Outdoor pool
9.8 out of 10, Exceptional, (99)
Refreshing dips in the seasonal outdoor pool complement indulgent spa services at this upscale bed and breakfast. After swimming, guests can relax by the firepit, explore the garden, or enjoy the acclaimed cooked-to-order breakfast.
$263 nightly
The price is $294
Nov 25 - Nov 26
Total with taxes and fees
The Inn at Stockbridge
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.

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.

Find out more about Lee

Discover top Lee attractions

Nestled in the scenic Berkshires, Lee, Massachusetts offers a tranquil escape for travelers seeking relaxation. Start your day with a visit to the nearby Laurel Lake, where you can unwind on the sandy shores or enjoy a leisurely swim in its crystal-clear waters. For a dose of culture, explore the Norman Rockwell Museum in Stockbridge, just a short drive away, showcasing the beloved artist's iconic works that capture the essence of American life. Nature enthusiasts can embark on a peaceful hike at the Beartown State Forest, where serene trails wind through lush forests and along sparkling streams. After a day of exploration, indulge in a rejuvenating experience at the Kripalu Center for Yoga and Health, offering a variety of classes and wellness programs. Staying in Lee not only puts you close to these calming activities but also allows you to relax in hotels that feature inviting pools, perfect for unwinding after a day of adventure. Many accommodations in the area prioritize quality and attentive service, ensuring your family feels pampered and well-cared for throughout your stay.

Find the best hotels with an outdoor pool in Lee

For travelers looking to enjoy a refreshing dip during their stay in Lee, Massachusetts, these hotels offer inviting outdoor pools and a range of amenities to enhance your experience.

Devonfield Inn B&B

  • Why it's great for poolside lounging: Devonfield Inn B&B is a haven for travelers seeking relaxation, an outstanding review rating of 10.0. The hotel features a stunning outdoor pool surrounded by sun loungers, perfect for soaking up the sun or enjoying a refreshing swim. Guests can also indulge in free breakfast options, ensuring a delightful start to each day.
  • Other amenities: This charming B&B offers a variety of features including a serene terrace, complimentary champagne service, and nearby golf course access. Guests can enjoy hiking or biking in the nearby area, indulge in daily housekeeping, and unwind in spacious rooms equipped with premium bedding and bathrobes. A kitchen and private picnic options add to the convenience, making it an ideal retreat for outdoor enthusiasts.
  • Nearby attractions: Housatonic River - 1.47 miles, Berkshire Mountain Country Store - 1.03 miles, Animagic Museum of Animation - 1.02 miles

The Inn at Stockbridge

  • Why it's great for poolside lounging: The Inn at Stockbridge is an exceptional choice for travelers who appreciate a touch of luxury alongside an outdoor pool experience. With an impressive review rating of 9.8, this inn combines elegance with comfort. Guests can enjoy the beautifully maintained outdoor pool, ideal for relaxation amidst the picturesque Berkshire landscape.
  • Other amenities: This charming hotel features a terrace and patio for outdoor enjoyment, as well as a 24-hour fitness facility for active travelers. Guests can pamper themselves with onsite spa services and massages, while the complimentary breakfast provides a delightful start to the day. Additional features include air conditioning, designer toiletries, and daily housekeeping to ensure a comfortable stay.
  • Nearby attractions: Housatonic River - 1.66 miles, Berkshire Theatre Festival - 1.28 miles, National Shrine of the Divine Mercy - 2.26 miles

Sunset Inn

  • Why it's great for poolside lounging: Sunset Inn presents a cozy option for travelers looking for budget-friendly accommodations with an outdoor pool. With a review rating of 7.6, this inn offers the perfect place to relax after a day of exploring the beautiful surroundings of Lee. The inviting pool provides a refreshing spot to unwind, especially in the warmer months.
  • Other amenities: Guests can take advantage of nearby skiing and hiking opportunities, with snowshoeing and sailing adventures just a stone's throw away. The inn is conveniently located close to sandy beaches and golf courses, ensuring plenty of outdoor activities are within reach. Self-parking is available for guests, making it easy to explore the area at their own pace.
  • Nearby attractions: Housatonic River - 0.07 miles, Berkshire Mountain Country Store - 0.61 miles, Animagic Museum of Animation - 0.59 miles

Top Lee Hotel Reviews

Explore a world of travel with Expedia