Hotels with a Pool in Stockbridge

Swimming becomes a highlight at this charming historic retreat where the outdoor pool invites leisurely afternoons. Beyond refreshing dips, guests savor excellent dining at 3 on-site restaurants, indulge in spa services, and discover adventure along nearby hiking trails.

Pool loungers invite blissful relaxation at this luxury bed & breakfast's seasonal summer oasis. Adventure seekers can enjoy kayaking, mountain biking, and fishing before returning to excellent breakfasts served in charming dining spaces.

Poolside relaxation awaits from May through September at this upscale bed & breakfast. After enjoying a delicious cooked-to-order breakfast that guests rave about, visitors can unwind with spa services or explore the garden and library.

Swimming options abound with 4 distinct pools, complete with loungers, umbrellas, and a poolside bar. Beyond swimming, families discover mini golf, volleyball courts, and seasonal activities from hiking to skiing at this recreational haven.

Splash into the consistently praised indoor pool, maintained at a comfortable temperature that delights families after Butternut ski adventures. Modern rooms with premium bedding await, complemented by a free breakfast buffet that earns glowing reviews.

Splash into the immaculate indoor pool after exploring nearby Ski Butternut slopes and Housatonic River Walk. Adventure seekers appreciate the hotel's proximity to seasonal outdoor activities, from snowboarding to mountain biking.

Swimming becomes a four-season pleasure with both indoor and outdoor pools surrounded by mountain scenery. Guests consistently praise the perfectly heated waters and relaxing hot tub after hiking local trails or skiing nearby Bousquet Ski Area.

Lounge by the inviting outdoor pool, where sun-drenched relaxation meets countryside charm. Beyond refreshing dips, this B&B delights with gourmet cooked-to-order breakfasts, bicycle rentals, and spa services for complete vacation bliss.

Sparkling waters welcome swimmers to this Berkshire retreat's indoor pool, where refreshing dips complement days of Tanglewood adventures. Friendly staff ensure exceptional service while a fitness center, bar, and coffee shop round out the experience.

Swimming enthusiasts splash in the pristine indoor pool while fitness buffs appreciate the adjacent workout center. Jae's Asian Fusion restaurant serves delectable meals just steps away from the water's edge, creating a complete relaxation experience in Lenox.

Mountain adventures begin at the seasonal outdoor pool, where refreshing dips follow hiking excursions. Complete with a rejuvenating sauna, this newly remodeled lodge offers delicious complimentary breakfast and cozy rooms with premium bedding for post-adventure recovery.

Poolside cocktails elevate summer afternoons at the seasonal outdoor pool, offering a refreshing complement to mornings filled with exceptional breakfasts. Friendly staff ensure a relaxing atmosphere throughout this cozy retreat near Tanglewood.

Refreshing swims await at the nearby outdoor pool after exploring Norman Rockwell Museum. Dog lovers appreciate the welcoming atmosphere, while skiers value proximity to Butternut. Newly renovated bathrooms and comfortable beds ensure a peaceful, clean stay.

Glide through the pristine indoor pool area, complete with comfortable loungers for post-adventure relaxation. Surrounded by outdoor recreation opportunities, from skiing to kayaking, this art deco hotel balances activity with serene comfort.

Swimming enthusiasts delight in the pristine indoor pool, available from morning until evening. After exploring nearby Tanglewood or hitting the slopes, guests rejuvenate in the soothing hot tub while friendly staff ensure a memorable stay.

Sparkling outdoor pool offers a refreshing escape among garden surroundings at this conveniently located Lenox retreat. Spacious rooms feature luxurious hydromassage showers or deep soaking tubs, making it a perfect base for Tanglewood Music Center visitors.

Splash into relaxation at the serene indoor pool, a perfect retreat after exploring nearby Tanglewood Music Center. Guests adore the firepit gatherings, complimentary continental breakfast, and manager's reception at this mountain sanctuary.

Sparkling waters await at the sun-drenched outdoor pool, surrounded by manicured gardens perfect for afternoon relaxation. Beyond the refreshing swim, guests appreciate spotless accommodations, helpful staff, and complimentary breakfast before exploring nearby attractions.

Poolside relaxation awaits at the seasonal outdoor pool, open daily from August through summer. Adventure enthusiasts can explore nearby skiing trails, sailing routes, and hiking paths before returning to comfortable, well-equipped rooms.

Sparkling waters beckon at the seasonal outdoor pool, open May through September for refreshing dips after exploring Tanglewood Music Center. Tennis enthusiasts appreciate the on-site court while garden and terrace views complete the upscale retreat.