Default HTG hotel image

Hotels with Swimming Pool in Southfield, Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Southfield Hotels with Swimming Pool

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Southfield hotels with a pool

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel room with two beds, a desk, a television, and a dresser.

1. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
P9,058
P10,117 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

2. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
  • Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.
P18,237
P22,006 total
includes taxes & fees
Nov 2 - Nov 3
The Old Inn On The Green
An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.
A breakfast area with a counter, coffee machine, and a display of pastries.
A modern bathroom with a large mirror, a sink, and a shower.
A hotel room with two beds, a desk, a TV, and a window with curtains.

3. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
P5,612
P6,268 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Great Barrington by IHG
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
A bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.

4. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
P11,948
P13,740 total
includes taxes & fees
Oct 18 - Oct 19
Blackberry River Inn
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.

5. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
P7,358
P9,448 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P9,932
P14,227 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

7. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
P7,899
P8,823 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A large house with a balcony and a grassy yard.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A two-story building with a gabled roof and a chimney.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

8. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
P6,509
P7,270 total
includes taxes & fees
Oct 22 - Oct 23
The Little Lion
A poolside area with lounge chairs and a pool.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

9. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
P17,876
P22,080 total
includes taxes & fees
Nov 10 - Nov 11
Prospect Berkshires
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

10. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
P9,590
P10,741 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
View all properties

Choose what matters most at hotels with a pool in Southfield

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Southfield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
Cynthia 1-night trip
Posted 14 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"Nice view and location for fall color."
Md 1-night trip
Posted 23 hours ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Wonderful"
Philippe 2-night trip
Posted 1 day ago
The Red Lion Inn
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Sitting around the fire pit after a long day of leaf peeping was glorious..."
Steve 2-night trip
Posted 2 days ago
Courtyard by Marriott Lenox Berkshires
Monument Mountain Motel

Monument Mountain Motel

8/10 Good
"Clean rooms. Good parking. Convenient location. Quiet."
Ricky 1-night trip
Posted 2 days ago
Monument Mountain Motel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"good location, friendly helpful staff"
Scott Patterson 6-night trip
Posted 2 days ago
Quality Inn Great Barrington
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."
Suzanne 5-night trip
Posted 2 weeks ago
Interlaken Inn & Resort

Frequently asked questions

What are some accommodations with pools in Southfield?
Quality Inn Great Barrington: Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak 'n Spruce Resort: Features a sauna, an outdoor pool, and spa services. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Provides a sauna, a seasonal outdoor pool, and daily. The Whitlock: Features a full-service spa, a seasonal outdoor pool, and 3 outdoor tennis courts.
What is there to see and do in Southfield?
Spend some time experiencing the great outdoors at Umpachene Falls Park and Rhodes Hill. During your stay, check out sights such as Suter Farm, Benton Hill, and Cookson State Forest.
When is the best time to book a hotel with a pool in Southfield?
Taking into account the local weather in Southfield is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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 28°F. The snowiest months in Southfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia