Vacation rentals in Pittsfield

Waterfront Cottage Private Dock | Kayaks | Rowboat

Super cozy, beautiful cottage on the lake & dirt roads.Yard: sitting areas, propane fire pit & grill, fenced in yard.Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided.

Value · Family · Check-in

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Location · Value · Comfort

Cozy A Frame Cabin

Discover Your Dream Getaway at Our Enchanting A-Frame Cabin in Danbury, NH! Hike lush forest trails, paddle across sparkling lakes, or hit the nearby slopes for seasonal adventure. After a day outdoors, kick back on the spacious deck, fire up the grill, and dine under the stars. Whether you're planning a romantic escape or a fun-filled family getaway, this hidden gem offers the perfect blend of comfort, charm, and natural beauty. Escape the ordinary—book your unforgettable Danbury retreat today!

Location · Family · TV

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Value · Family · Grill

The Vineyard Penthouse - Beautiful Inside & Out

Wake up to rows of sun-kissed grapevines and unwind in a serene, vineyard-view retreat. This open-concept suite featured a plush king bed, abundant natural light and inviting modern décor. Sip wine at sunset, cook in the well-equipped kitchen, or unwind and relax, in our new “shared” hot tub. Although there are other guest on the property you will have this space to call your own and enjoy. ~ 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 20 min to Gunstock and 25 min to Bank of Pavilion

Location · Family · Amenities

Antq. Farm Ell-Private deck/views/trails/Dog yard!

This farmstead "ELL" has 1800's character, yet updated for modern day. WiFi & AC! We hope this space inspires. Orig. hand hewn beams, pine floors, woodstove & vntg. bath tub to warm you after a day skiing or family sliding down threw the fields. Mtn. bike or walk the trails. Prvt. deck w/grill, fenced yard, firepit & views. We are open year round @ "Windy Ridge Inn" Nh snowmobile trails at your door! UNH, Dell Lea, Gunstock Mt, Laconia, Atlantic Ocean, NH lakes, ME Outlets. 90 min to Boston

Location · Family · Getting around

The Barnstead Train Depot 1889

Romantic and cozy 1 bedroom home in Barnstead, New Hampshire. A former train depot built in 1889, this historic home stands on the banks of the Suncook River Reservoir. Enjoy private dock access for fishing, swimming, canoeing and kayaking. Immerse yourself in nature on a walk through the woods on the attached rail trail. Enjoy sunsets and river views directly from the deck. When the sun goes down be sure to stick around to view the blanket of stars that have blessed the Depot for 136 years.

Value · Location · Heating

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

This romantic & family-friendly lakefront chalet comes with a private beach, hot tub, kayaks & stunning views and is packed with amenities. It’s a serene home base to explore some of the best New England towns and is in the heart of the Lakes Region. Swim, kayak, bike a scenic trail, fish, hike, explore historic towns, farms & food scene, or simply grill with a view & play board games. We have poured our heart into making this a romantic yet very kid-friendly retreat (kids gear included).

Location · Family · Sleep quality

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Value · Family · Decor

Farmhouse Apartment with Scottish Highland Cows

Craving a break from the chaos of your life? Wake up to breathtaking sunrise views, and watch cows grazing outside your window. Feel the stresses of life melt away. Our hilltop farm provides the perfect setting to connect with cows, find inner peace, and unwind. Leave behind worries, arguments, and the hustle. At my farm, the only thing on your to-do list is relaxing and creating memories.

Location · Family · TV

Waterfront | Sunsets | Kayaks | Chef's Kitchen

Waterfront escape on Huntress Pond. This spacious 2-bed/2-bath home features a private dock, kayaks, canoe, and a spacious deck for sunset evenings overlooking the water. Cook with local farmstand finds, dine outdoors, and unwind under the stars. Alton Bay is 20 min away; Concord, Wolfeboro, Laconia & Tilton ~30 min; Gunstock 35 min. Local hidden gems shared in the guidebook.

Location · Family · Condition

Pastoral Farm in NH

Cozy private get away. A little bigger than a tiny house, apart from the main farm house and barns on a beautiful hill top setting. Sit and relax , take a walk through the fields or if your feeling a little more adventurous explore the beaver pond or hike out to picnic rock. This is country living in NH. *Please note that we are 8/10ths of a mile out on a dirt road.

Family · Location · Condition