Vacation rentals in Phillipston

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Family · Location · Hospitality

Otter's Paradise

Welcome to our luxurious lake house in Gardner, Ma! Located on a quiet private pond, this home feels just like a hotel while letting you enjoy the lake life. The house is cozy and well-furnished, offering beautiful views and a peaceful space to relax. You can enjoy fun outdoor activities like kayaking or fishing, simply unwind on the deck. 10 min away from Mt Wachusett, you can hit the slopes, hiking, nearby, you'll also find exciting activities like skydiving, ice skating, at trails and more.

Family · Location · Backyard

Stone n' Sky Lodge

Complete with all the comforts & amenities of home, Stone n’ Sky Lodge is fully furnished & decorated with family heirlooms & fine art. Featuring a fully equipped kitchen, fiber optic internet & a separate home office, the Lodge is located on a paved, dead end road, surrounded by a wildlife sanctuary; yet minutes from town & interstate highways. Local attractions, festivals, artisans, hiking, micro-brewed beers, ciders, good food & music are all to be discovered within minutes of this location.

Location · Value · Pets

Wild Blueberry Farmhouse: Nature & Sports!

Welcome to Wild Blueberry Farmhouse, your private spring retreat in the heart of nature! Our home is the perfect place for families and friends to relax, unwind, and reconnect. Enjoy the warmer weather on our professional tennis, pickleball, and basketball court. Take a peaceful hike on the nearby trails. In the evening, gather around the outdoor fire table for s’mores and stargazing. Don’t miss the spring events at the Red Apple Farm, ranked among the best orchards in the country by USA Today!

Location · Family · Accuracy

The Film Shack: A Sweetwater Stay

Located on the shore of Tully Pond, The Film Shack is a newly designed water front vacation home with breathtaking views of Tully Mountain. This 4-season home features four bedrooms, a screening room, a video game nook and a bonus guest cottage. The personal home of filmmakers Patti Moreno and Robert Patton-Spruill, it is decorated in the "Atomic Age" style. Maple floors, aviation, and cargo style furniture, stainless steel bathroom and kitchen with a wood stove for those chilly fall mornings.

Location · Value · Bathroom

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.

Family · Location · Hospitality

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

Family · Value · Amenities

Dwelling Place

Welcome to Dwelling Place Unwind at our peaceful, open-plan carriage house apartment, tucked away on thirteen wooded acres. Seeking adventure or relaxation, this is your perfect escape. Minutes from recreation-rich lakes and trails of the north Quabbin; easy access to hiking, kayaking, leaf peeping, and snowshoeing. Also close to golf, disc golf, and an equestrian center. Return to tranquility to rest, recharge, and experience a true retreat in nature—perfect for all seasons.

Value · Family · Backyard

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Value · Family · Kitchen

Our Pondside Cabin

Charming log cabin retreat equipped with modern amenities and conveniences! Just 3 minutes from Wachusett skiing/hiking, 8 minutes to Great Wolf Lodge and 9 minutes to Harrington Farm. Whether you're planning a peaceful retreat or an active adventure, our cabin offers the best of both worlds. Book your stay today and experience the perfect blend of rustic charm and modern comforts. We can't wait to welcome you to our happy place!

Family · Value · TV

Cottage @ Partridge Pond

Relax on Partridge Pond. Great for paddle boarding and swimming or just hanging out on the deck/dock and grilling. Great local restaurants and Wachusetts brewery 5 min up the road and Wachusetts ski area 10 min away. Local hiking trails and golf course nearby. Newly furnished. Updated utilities. Quiet area and a great retreat. Year round entertainment. We enjoy our time here. This is a ‘pet-free’ property.

Value · Location · Getting around

Rustic cabin with A/C at historic orchard & cidery

Escape to the serenity of Western MA—perfect for couples, nature lovers, cider connoisseurs, and adventure seekers (dogs welcome too). Each season offers something different, from apple picking and crisp fall walks to cozy winter stays, spring blossoms, and summer days spent hiking, kayaking, or relaxing by the fire under the stars—with a unique orchard and cidery experience just steps away.

Location · Family · Nearby