Vacation rentals in Orange

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

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

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.

Beautiful timber-frame treehouse

The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.

Panoramic Sunroom | Soaking Tub | Modern Cabin

Located on a large serene pond, The Retreat at Eagleville is perfect for fishing enthusiasts, nature lovers, family fun, and anyone looking for an escape from the hustle of the city. Enjoy glamping amenities including a soaking tub, fully-equipped kitchen, outdoor BBQ & griddle, and a covered pavilion with picnic table. Relax by the firepit, unwind in the hammock, or lounge in Adirondack chairs. ☞ Complimentary wood for 1st fire ☞ No checkout rules ☞ Linens provided ☞ Self Check-in

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Artsy Pine Cabin in the Woods

Come relax in our private and cozy one room cabin tucked in the woods on the family homestead. A peaceful location for connecting with nature, writing & hiking. It's a 12'x16' cabin, with a comfortable queen size bed, electricity, mini refrigerator and electric kettle. Water is provided. Equipped with a clean outhouse and an outdoor hot shower on side of main house. ( May use indoor shower in main house in cooler months) Excellent spot for star gazing.

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.

The Fishing Cottage: A Sweetwater Stay

Located on the shore of Tully Pond, The Fishing Cottage is a designed vacation home with breathtaking views of Tully Mountain. This 4-season Cottage has real salvaged barn wood walls; up-cycled maple floors and one-of-a kind scratch built furniture and lighting fixtures. The deconstructed architecture leaves exposed the electrical conduit and copper plumbing pipes, making the cottage feel alive and organic.

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.

Enjoy your stay in an Antique Home in a Toy Museum

Stay on the second floor of a 1780 Colonial House in a very unique toy museum. Winchendon is a quaint bedroom community known as "Toy Town". Located close to hiking trails, skiing, and lakes. The home is located right downtown, close to restaurants, bike trails and the library. You have access to a kitchen, 1 full bath, and 2 half baths. All rooms are well appointed, and period decorated.

Carriage House at Revival Wheeler Mansion

This newly renovated carriage house is situated behind the historic Wheeler Mansion in downtown Orange, convenient walking distance to shops and restaurants. This 2 level house has a full kitchen, full bathroom, open floorplan kitchen and living room, 2 bedrooms and balcony deck on the upper level and one bedroom on the ground floor with parking.