Vacation rentals with outdoor seating in Walpole

The SugarShack at Sweetwater

Welcome to our off-the-grid cabin, sleeping 2-4 people with an upstairs loft & downstairs custom Murphy bed. It's equipped with lights, mini-fridge, Bluetooth speakers & an indoor/outdoor bar. Outside you'll find a private fire pit & charcoal grill, a shared outdoor kitchen pavilion w/ gas grill (stocked with cooking supplies) & the outdoor bathroom w/ a real flushing toilet, sink and outdoor shower. Access the Tooky River just steps away and enjoy plenty of space, privacy & beautiful scenery!

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.

Secluded Renovated Retreat Surrounded by Nature

Get away from it all in a secluded, yet modern cabin, which guests have loved for its "silence and beauty" and called "peaceful" and "serene". Located on the Lakefalls Estate, which maintains the roads, Mended Oar features heated floors throughout, a well-furnished kitchen with quality appliances and equipment, and luxurious linens. Hike the many trails outside the door on the snowshoes you'll find, then come inside to enjoy the wood burning fireplace (wood provided) and play a board game.

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Vermont Treehouse - Romantic Private Elegant

3 night minimum, unless prior approval, self checkin. Work remotely. This romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

Quiet House in the Woods

Relax with the whole family at this peaceful place to stay. - Gregg Lake 5 mins away (Swim, Volleyball, Swings, Boat Docks) - Great hiking trails (Monadnock & Miller State Park) - Ski in the winter (Crotched Mountain 20 mins away, Pats Peak 30 mins away) - Small town: Mom & Pop shops/restaurants, Antique stores - 2 Decks: Out door dining & sitting areas This is not an investment property, this is my home. Please be respectful of the property. Thank you! Hope you enjoy your stay!

Private Hot Tub Suite

The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Fire Pit, Grill, Hammock, Gym equipment Xbox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong tables, mini pool tables Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, backyard on 2 private acres

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Triggers Cabin

Cabin in the woods on a stocked trout pond. Outside deck over the pond for quietly relaxing. Outside fire pit. Gas grill. Inside fireplace.Located in a small private quiet campground. On 200 acres of private wooded land in central Massachusetts. Located on hiking trails that are also used for biking & horseback. Bring your own linens....but kitchen fully equipped. A great place to enjoy the out doors & disconnect & recharge..