Vacation rentals in West Dudley

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Woodstock Red Barn | Private Apt in Idyllic Town

This studio apt offers you a comfortable & quiet stay in pastural Woodstock. Surrounded by rolling hills & dairy farms, this spacious & completely private apt is the perfect place for a weekend retreat. Whether that means exploring the quaint towns that make up the quiet corner or taking time to escape the day to day & recharge, this rental has you covered. You will enjoy complete privacy in this detached dwelling w/ a private entrance & self-checkin. It also features free parking, WiFi & A/C.

“Tranquillity on the Lake ” Woodstock Valley, CT.

Summer is here !! Enjoy fun relaxing water activities on beautiful Lake Bungee. Enjoy direct waterfront sunrises , 1400 sq ft. Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the stars. BBQ propane grill. Stroll around both lakes, see bird sightings,nature’s at its finest. Great local dining & wineries. Each season paints its own stunning beauty. Relax and enjoy Tranquility

Luxe, private, separate Suite in peaceful setting!

Calendar just opened for May & June! Luxurious, sun-filled 1-BR In-Law Suite with private bath, Living Room, Porch & separate entry. Country setting 2-minutes from one of North America's "Top 10 Scenic Byways!" Living Room w/ paneled fireplace, screened Porch, equipped Kitchen. Spacious tiled Bath with shower. Inviting bluestone Patio & heated, gunite salt-water pool. Near farms/markets, antique shops, restaurants. Centrally located 1-hour from Boston, Hartford, Providence & the CT Shore!

Brookside Chalet

Not just a place to stay but a place where you will want to stay. - Dedicated parking space - Well-appointed full kitchen - Deck overlooking Mashamoquet Brook (our guests refer to it as the tree house:) The bed will be the highlight of your experience. This high quality queen is accessorized with a pillow top mattress, goose down and memory foam pillows and spa quality sheets and pillow cases. Location: - Five minute drive to Pomfret Prep. - Ten minute drive to main Street in Putnam.

Main Street Suite

Enjoy a boutique hotel experience in a historic New England town. This private, well-equipped suite is housed in a mixed use building (with a few small businesses with daytime hours) next door to a popular craft beer pub, and across the street from a hopping neighborhood Japanese restaurant. Enjoy everything you need in a home base with quick access to Old Sturbridge Village, lakes, trails, wineries, breweries, restaurants, farmers’ markets, festivals, events, antiquing, and more!

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.

Enjoy a Farm Stay without the Work

This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.

1 BR on Webster Lake.

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.