Holiday rentals in Lake Chaubunagungamaug

The Tree House at Underhill Hollow

The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.

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

Beautiful, Unique, & Cozy Cedar Flat

Come enjoy this new and beautifully designed space in historic Uxbridge, MA. Set up like a tiny house, it is the most cozy and clean place you will visit. A ship’s ladder will take you to the queen loft bed or use a new PotteryBarn sleeper sofa. The Frame TV will act as a beautiful painting if you prefer to "unplug." Climate control and a hammock chair are a perfect combo! Located on a quiet street, it is an easy 25 min. drive to Providence or Worcester, and only 50 min. to downtown Boston.

Trees, pond, and wildlife in its entire splendor

Charming, comfortable and convenient, located in a quiet corner of Connecticut. Front door private entrance. Second floor you have privacy and 3 bedrooms available,2 full baths, walkin closet, and hardwood floors. On the first floor, you have a 14F x 15F room that can be used as a living room or kitchenette or TV room. Your living room has a mini fridge, microwave, coffee maker, large TV, surround sound system. Other amenities include. 24 hour check in/free coffee, free snacks, high speed wi-fi.

“Tranquillity on the Lake ” Woodstock Valley, CT.

WINTER WEEKLY & MONTHLY DISCOUNTS.The beauty of the serene winter awaits you. Featuring your own private direct waterfront with 1400 sq ft.of indoor living space . Queen bed in Master Suite. Queen sofa in living area,Indoor propane fireplace,full stove, full refrigerator, microwave. Enjoy your own deck, propane fire place.Sway on the swing , gaze at the stars.Stroll around the lake, see local birds. Great nearby dining,wineries,breweries . Enjoy this winter and embrace the joy of lake living !!

Rustic Farmette Studio w/yearround Hot Tub

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

Artist studio in the woods

Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quite, tranquil, relax. As of 1/1/26 booking rate will be $120 per day. Pool $20 seasonal.

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

Webster MA on the Lake 1 Bedroom.

Lake Chargoggagoggmanchauggagoggchaubunagungamaugg. Private entrance. Enclosed porch right off the living area with 3 booths for crafting, eating and relaxing. An open patio & small yard space for games & picnic table and a solo stove. 80 ft of shore line, which is ideal for kids swimming/fishing, a beach toilet & gazebo. 4 Kayak's, 2 paddleboards, and a pedal boat are available for guest use with swimming ability.

Lakefront Beauty with Hot Tub

Relax and recharge at this beautiful lakefront home with 2 bedrooms, 2 baths, and room for 6. Enjoy the hot tub, a private gym, kayaks, paddle boards, and a large deck with grill and patio seating. Play yard games like giant Connect 4, or head to the garage for a ping pong match. End the day by the fire pit under the stars. Perfect for families, couples, or friends seeking fun and tranquility.

Treehouse - Countryside - Farm Animals - Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)