Vacation rentals in Pittstown

Whimsical Carriage House & Private Courtyard

Welcome to your boutique retreat in the heart of downtown Troy! This cozy second-floor studio, designed by a local artist, is tucked away in a standalone Carriage House with a private entrance next to a whimsical mural by local artist Kayla Ek, and a lush New Orleans-inspired courtyard. Just steps from Troy’s best dining, art, nightlife, and wedding venues—and less than a block from the RPI approach—this gem is perfect for a romantic getaway, solo escape, or stylish stay while visiting the area.

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Mountain View Glamping Cabin

Experience ultra-glamping at this brand new off-grid cabin, and pergola with an outdoor kitchen and sleeping loft. Relax, unplug, sit back and enjoy the view, the hawks circling above, a crackling fire, your favorite beverage and if you want, your two best friends to join you. It's up to you who gets the cabin, and who gets the sleeping loft - each have a comfy queen bed and both come with an amazing view. This is glamping, but in regal style, dog friendly and loaded with amenities.

Cozy, Cool & Comfy, 1860s Troy 1BR Apartment #2

Make yourself at home in this sunny , fully furnished 1BR on a quiet street in Troy’s Lansingburgh area. Off-street parking, WiFi, and a fully equipped kitchen will make this your perfect home away from home in a historic mid-1800s farmhouse. Enjoy all that Troy and the region has to offer: events, restaurants, and shops, mere minutes to any other local destination. The huge, quiet yard is the perfect place to spot roaming deer, rabbits and birds, work, or just grill and chill!

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Irish-Inspired Hunt Box Retreat for Horse Lovers

Set on 38 acres, the home is influenced by Irish equestrians. Its owner Kelli spent time learning from some of the best horseman in Ireland who resided in their own “Hunt Box”or small living quarters connected directly to the barn. The large floor to ceiling windows allow you to experience watching the horses in their natural state. The space provides guests with the small, simple and beautiful moments of being an equestrian. This is an unforgettable experience like no other.

Lovely Loft in Downtown Troy

This beautiful loft space provides a unique getaway in Troy. It’s walking distance to RPI, Russel Sage, EMPAC, The Troy Music Hall, the Troy Farmers Market, and many of Troy’s restaurants. This is a studio apartment with a king size bed, wifi, kitchen with an electric cooktop and stand-alone shower. ***Important Accessibility Note*** While this space comes with beautiful views of nearby churches, it is located on the fourth floor with a very steep three flight walk up.

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Adorable Apartment - Near Emma Willard, RPI, Troy

Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

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

Escape to this family-friendly Clifton Park retreat—just 20 mins to Saratoga Springs and 25 to Albany. Perfect for fall getaways with a fire pit, outdoor movie screen, private playground, basketball court, and garden. Features a king bedroom, home office, full kitchen, fast Wi-Fi, soaking tub, and 20' x 55' parking for RVs or boats. Relax in the crisp autumn air, enjoy backyard movie nights, and stay productive or cozy in a quiet, peaceful neighborhood.

Airbnb @ Sweet & Savory Farmette

Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.

Overlook at Graceful Acres Farmstay

Enjoy the grace of a historic family farm in the heart of eastern NY. Let the cool, fresh air and sounds of the outdoors start your day. Fill your time with a hike across our 440 acre farm then spend time with the animals and learn more about regenerative farming during a scheduled farm tour. Graceful Acres Farmstay is situated an hour south of the Adirondack State Park and within 35 minutes of Saratoga Springs, Albany, Troy, NY and Bennington, VT.