Vacation rentals with a pool in Rensselaer County

4.94 out of 5 average rating, 162 reviews

A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.

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.

4.88 out of 5 average rating, 17 reviews

A cozy living area features a comfortable couch adorned with soft pillows, complemented by a wooden coffee table. An adjacent kitchen area with modern bar stools offers ample space. Natural light flows through the open layout, and a staircase leads to an upper level.

Apartment in Hancock

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Stylish 1BR, 1BA suite with an additional Pull Out Queen sleeps 4 comfortably. It sits RIGHT in the Thatcher Building in front of the MAIN ski lift in Village Center. You can not get better than that! All the convenience without the bustle. This large 650 sq ft condo features brand new decor meticulously maintained, and includes a full kitchen with all the amenities. As a guest, you will

5 out of 5 average rating, 9 reviews

Home in West Sand Lake

Farmhouse at June Farms

This property is the perfect stay if you are looking to visit June Farms and need more space than The June Farms cabins are able to accommodate. The view from the kitchen is something out of a Norman Rockwell painting. Your Stay Includes: * 3 Bedrooms * 2 bedrooms with plush king beds * 1 bedroom with a queen on queen bunk beds * 3 Full Bathrooms * Plunge Pool – cold pool in the summer, hot tub in the winter * Theater Room * Outdoor Patio & Grill * Central Air & Wi-Fi * Chef's Kitchen

The exterior of the condo is shown covered in a blanket of fresh snow, emphasizing its charming, sloped roof. A snow-laden evergreen tree stands nearby, while a gently sloped pathway leads to the entrance, inviting guests to explore the winter landscape.

5 out of 5 average rating, 11 reviews

LuNo - Relaxing Ski and Culture Berkshires Escape

Insta: @LuNo_Airbnb Welcome to our dream ski getaway! This renovated home “LuNo” is ideal for up to 8 guests, featuring 3 bedrooms, 2 baths, and all comforts for a perfect Berkshires getaway. Cozy living area with smart TV, a fully equipped kitchen, and a private patio with a grill. Just 2 miles from Jiminy Peak and close to Tanglewood, Mass MoCA, and The Clark Museum, this condo offers both adventure and relaxation. Unwind at the community pool in summer and enjoy scenic beauty year-round.

A peaceful scene reveals a winding road leading through a residential area with well-maintained homes. Snow-covered mountain slopes are visible in the background, flanked by trees that display early signs of changing seasons.

4.92 out of 5 average rating, 109 reviews

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

4.99 out of 5 average rating, 70 reviews

An outdoor scene features a clear blue sky above a heated saltwater pool set within a spacious green yard. Surrounding trees provide a natural backdrop, and a small shed is visible next to the pool, which is enclosed by a wooden fence.

Home in New Lebanon

Berkshire Mountain home views, pool, Queechy Lake

Note: pricing includes all fees such as cleaning and air bnb services charges! Happy to break it down for you before booking. Serene house on 11 acres, surrounded by farmland. Perfect for families to share! Enjoy beautiful view of Berkshire mountains while sitting on expansive deck or in bright,sunny screened-in sunroom. Heated, 20x40 inground salt water pool. Membership to Queechy Lake included! Walk to Corkscrew Rail trail, 5 miles of flat, wooded trail for walking and biking.

5 out of 5 average rating, 49 reviews

Aerial view of a log cabin surrounded by a lush green lawn and wooded areas. The spacious front yard features a meandering pathway and mature trees, while the cabin's expansive porch and roof are visible against the backdrop of a clear sky.

Cabin in Sand Lake

"The Cabin" - Cozy & Rustic Home (Averill Park)

This luxurious log cabin, nestled on 200+ acres of private, expansive wilderness, is the perfect escape. Enjoy sunrise from the front porch, grill on the back deck and explore the 18-hole disc golf course, croquet court, swimming pool (June-September)and multiple walking trails throughout the forested property. Jiminy Peak Ski Resort, the Berkshires, and Saratoga Springs are all nearby. All amenities are provided with a personal touch that will make your stay relaxed and memorable.

A snow-covered entrance showcases a wooden sign featuring 'SMITH UNITS 1061 - 1064.' The residential building, adorned with white siding, includes a window unit air conditioner protruding from the wall. Surrounding shrubs are blanketed with fresh snow.

4.83 out of 5 average rating, 103 reviews

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

4.92 out of 5 average rating, 103 reviews

The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

4.96 out of 5 average rating, 55 reviews

The open living area showcases a modern curved sectional sofa in dark leather, adorned with cream and patterned pillows. A sleek chandelier hangs from the high ceiling, complemented by a wall-mounted TV and a wooden fireplace. Large sliding doors lead to the outdoor patio.

Home in Hancock

Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

5 out of 5 average rating, 11 reviews

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure ★☆ ABOUT THIS SPACE ☆★ Welcome to Jiminy Peak Slopeside Getaway, your all-season mountain retreat. Enjoy scenic views and a true ski-in/ski-out experience—just a 3-minute walk to the chair lift at Jiminy Peak. This 2-bedroom, 2-bath home sleeps up to 7 guests and offers private parking, a porch, and a deck, plus access to a heated pool, indoor/outdoor hot tub, and clubhouse.