A diner with a green roof and a red barn in the background.

Find Hotels with a Pool in Spencertown, NY from CA $107

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Check availability on Spencertown Hotels with a Pool

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Spencertown hotels with a pool

Outdoor pool
Exterior
Front of property
Lobby sitting area

1. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
  • Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
CA $96
CA $107 total
includes taxes & fees
Oct 5 - Oct 6
Berkshire Travel Lodge
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.

2. 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.
CA $169
CA $189 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

3. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
CA $153
CA $171 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
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 bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

4. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
CA $147
CA $164 total
includes taxes & fees
Oct 21 - Oct 22
The Little Lion
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.
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.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
CA $252
CA $352 total
includes taxes & fees
Oct 19 - Oct 20
The Red Lion Inn
A poolside area with lounge chairs and blue umbrellas, surrounded by 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.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A house with a stone patio and wooden stools.

6. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
CA $254
CA $284 total
includes taxes & fees
Oct 4 - Oct 5
Little Cat Lodge
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A garden with wooden Adirondack chairs and a stone pathway.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
CA $112
CA $157 total
includes taxes & fees
Oct 19 - Oct 20
Berkshire Mountain Lodge
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A bathroom with a white sink, mirror, and toilet.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
CA $112
CA $125 total
includes taxes & fees
Oct 5 - Oct 6
Howard Johnson by Wyndham Lenox
Pool
Exterior
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

9. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
CA $173
CA $193 total
includes taxes & fees
Oct 20 - Oct 21
Hampton Inn & Suites Berkshires-Lenox
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.

10. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
CA $166
CA $213 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Club Vacations Oak 'n Spruce Resort
View all properties

Choose what matters most at hotels with a pool in Spencertown

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Spencertown Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"This was a nice clean convenient hidden gem. Situated on the water, a little cool right now , but the beginning of fall follege was very pretty. Staff was polite and helpful. I would return."
Anthony 2-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 2 days ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 2 days ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice room. Exceptionally clean. Great staff"
Daniel 3-night trip
Posted 2 days ago
The Yankee Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 11 days ago
Howard Johnson by Wyndham Lenox

Frequently asked questions

What are some accommodations with pools in Spencertown?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Quality Inn Great Barrington: Provides a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Features a steam room, 3 indoor pools, and spa services. Pocketbook Hotel and Bath: Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
What is there to see and do in Spencertown?
Make a point to visit attractions like Berkshire Botanical Garden and Mahaiwe Performing Arts Center. During your stay, check out sights such as Norman Rockwell Museum, Catamount Aerial Adventure Park, and Stockbridge Bowl.
When is the best time to book a hotel with a pool in Spencertown?
Taking into account the local weather in Spencertown 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 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Spencertown are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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