Pittsfield : locations de vacances avec piscine

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.

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. 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.

*Discount * Berkshire’s Sweet SpotPool/Spa TWood

The Berkshire's Sweet Spot 2 property is an entire half of a duplex apartment located in central Berkshire County within walking distance to downtown. Renting both sides of the home may be an option. They are recently updated for your comfort with newer kitchens, baths and new smart televisions. The location can't be beat for seeing all of the Berkshire's attractions. The neighborhood is very peaceful, quiet and safe. Enjoy your own private oasis with seasonal in ground pool and year round Spa!

Pool, Farmhouse, Pets Welcome at Roundhill Farm

An historic 1750 farmhouse on a quiet, beautiful 120 acre property. Huge rooms with wide plank original flooring, 6 bedrooms, large family room with fireplace, kitchen, dining room, and formal living room. The property includes a pond which you're welcome to skate on in the winter, and a horse barn and pastures. In the summer you'll have access to our in-ground pool. We welcome your pets! Come ski Jiminy Peak, only a 25-minute drive from this airbnb! The house sleeps 11 people comfortably.

Restored 1735 Granary I Mountain Views + Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 20-ft cedar-lined ceilings, original wide-plank pine floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to Lenox, Tanglewood, scenic trails, and local farms. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

Stylish Rural Sanctuary! (+ Summer Pool)

Recently re-opened for short term stays! Just minutes from Chatham, NY, and nestled in the heart of the Hudson Valley, this serene home on over 8 acres offers breathtaking mountain views. Impeccably renovated in 2022, it seamlessly blends the charm of 18th-century Shaker architecture with the sleek elegance of modern Scandinavian design. Indulge in lightning-fast fiber internet, large smart TV, top-tier appliances, including a Miele fridge, Bertazzoni stove, Bosch dishwasher, and more!

Grand Berkshire Manor By Evergreen Home

Welcome to The Manor – your refined escape to the tranquil beauty of the Berkshires. Discover a perfectly situated, spacious retreat in the heart of the region. This elegantly appointed five-bedroom / 4.5 bathroom home offers serenity, comfort, and style — complete with a private pool, peaceful surroundings, and effortless access to iconic destinations like Tanglewood, Mass MoCA, The Norman Rockwell Museum, premier ski resorts, and acclaimed dining experiences.

Near Saratoga – King Bed, Tub, Fire Pit & Movies

Family-friendly Clifton Park apartment near Saratoga Springs (20 min), Schenectady (20 min), and Albany (25 min). Enjoy a fire pit, outdoor movie screen, basketball court, private backyard playground, garden, and a dedicated office for remote work. Includes 1 oversized bedroom, full kitchen, soaking tub & shower, fast Wi-Fi, washer/dryer, and a 20' x 55' parking pad for RVs, trailers, or boats. Quiet cul-de-sac, full guest access, and self check-in.

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3 - 5.