Vacation rentals with a pool in Pittsfield

4.95 out of 5 average rating, 136 reviews

Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

4.95 out of 5 average rating, 131 reviews

Tiny home in Ghent

Country Getaway Tiny House in Woods w/Pool/Sauna.

Tiny Small House - 600 Sq ft. of new living space on 30 private acres with walkable trains in Beautiful Columbia County. Secluded privacy surrounded by nature. House has everything you need and sleeps 4 with two twin loft beds. Enjoy the pool and renovated barn pool house. In the Winter stay warm by the wood stove. Enjoy the 6 person sauna year round. Restaurants close by or stay in and enjoy the property. Located 9 miles from Hudson and 3 miles from Chatham and Kinderhook. Near OMI Arts Center.

4.97 out of 5 average rating, 37 reviews

Home in Colonie

Adorable house with pool

Beautiful neighborhood home on a quiet dead-end street! and minutes to from airport. Restaurants, groceries store and the regional mall all within minutes!!! This wonderful spacious and family-friendly house offers you: - 3 Bedrooms with comfortable beds! - 2 full Bathrooms - Fully stocked Kitchen along with a dining area - washer and dryer - private in-ground salt water pool - Outdoor patio *Note the pool is open between Memorial Day until Labor Day, under responsibility of the guest.

4.94 out of 5 average rating, 125 reviews

Home in Germantown

Hilltop modern with stunning mountain views

Beautiful modern residence with a pool & fireplace in Germantown. Fantastic as a weekend getaway or longer-term rental. In the front, stunning mountain views wrap around the master bedroom, kitchen, living room and deck. Out back, a spacious yard and rolling hills. Grill & eat on the big pool deck, lounge in chaises. Fully equipped kitchen, washer & dryer, and *fast wifi*. Perfect for remote work, and each space has its own desk. Shop, walk, hike, ski: Close to Hudson, Olana & Catskills.

5 out of 5 average rating, 4 reviews

Home in Egremont

Fabulous Heated Pool, Screen Porch, Ping Pong!

Stone Hill is an immaculate property with big views! Amenities include: 3+ bedrooms, 3 full baths, sleeps 9 max. High speed internet/wifi, central AC, lovely gas fireplace, all stainless Bosch appliances and a gas range, heated pool with several areas of outdoor furniture, propane BBQ grill, sun deck, 3-season sunny screened porch/sunroom, 2-car garage, gym, ping-pong table, washer/dryer, portable crib, high chair and more! Pet friendly for non-shedding hypoallergenic pets only with pet fee.

4.93 out of 5 average rating, 243 reviews

Home in Hudson

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

4.96 out of 5 average rating, 348 reviews

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

4.95 out of 5 average rating, 211 reviews

Townhouse in Hudson

Palazzo Hudson: Luxury Home with Pool, Spa, Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & a separate poolhouse library lounge. A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

4.85 out of 5 average rating, 26 reviews

Home in Valatie

Beautifully Designed 4BR Home | Heated Pool+HotTub

This hilltop house sits secluded above Kinderhook Lake, offering a peaceful escape with/ elegant interiors and lots of natural light. Cozy up by the fireplace, cook in the fully equipped kitchen, or unwind by the heated pool and hot tub. Enjoy this luxury retreat in the scenic Hudson Valley. *Enjoy 3.5 acres of privacy/breathtaking scenery *Heated pool & hot tub *Spacious basement w/ gym, pool table & cinema setup *Cozy living room w/ fireplace *Near Hudson & Jiminy Peak ski resort

4.9 out of 5 average rating, 41 reviews

Cabin in Valatie

Private Cabin in the Woods w/ Hot Tub near Hudson

This spacious cabin-style home is surrounded by towering trees. It's perfect for escaping from your worries and enjoying nature at its finest. Venture out to Hudson, NY, where you can find many great restaurants and bars, or explore Hudson Valley's best hiking trails, and scenic views just minutes away. Whether you're looking to unplug from technology or work on your next great novel or chill with the family, this place has everything you need to get away from it all.

4.97 out of 5 average rating, 70 reviews

Home in Athens

Lake House with Game Room

Relax with the whole family at this peaceful place. As a guest you'll have access to our Sleepy Hollow Lake community beach area, pools and playgrounds, and pickle-ball, tennis and basketball courts. Athens hosts a gourmet bakery, restaurants and an award-winning brewery. Drive 7 miles to explore historic Catskill, 12 to hip Hudson and for year-round sports enthusiasts - only 30 to Windham and Hunter Mountains. Game room with pool table, shuffleboard and bowling!