Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

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Top guest favorite

A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.

Cottage in Northwood

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.

4.94 out of 5 average rating, 159 reviews

Top guest favorite

An aerial view showcases a house positioned along the shoreline of Northwood Lake. The private lot is surrounded by lush trees, with a spacious wooden deck and two docks extending over the water. The landscape offers a serene environment perfect for outdoor activities.

Home in Northwood

Deja Blue Lake House

Enjoy a whole house that sits directly on Northwood Lake on a private lot. House has 4 bedrooms and 1 1/2 bathrooms. 1st Bedroom has a Queen size bed, 2nd Bedroom has a Queen size bed, 3rd Bedroom has a Full size bed, 4th Bedroom has a bunk bed which is a Full Xl over a Queen.There are 2 docks. Bring your boats, floats, jet ski's, fishing poles, etc. The boat launch is located within walking distance. We have 4 paddle boards, floats, and a kayak for use while there. We do have some life jackets.

5.0 out of 5 average rating, 30 reviews

Top guest favorite

An aerial view of the equine estate showcases a blend of green fields and autumn foliage. The main building, featuring a dark roof, is bordered by trees and leads to a well-maintained driveway. Nearby, two red barns complement the rural landscape.

Farm stay in Loudon

Unique Equine Estate w/an Indoor Pool & Hot Tub.

One of a kind equine estate w/indoor pool, hot tub, billiards, cooks kitchen, new TVs & upgraded internet. The 4 bdrm, loft & common areas sleep 17 ppl. and w/6,000 sq. ft. everyone will have space to relax. This estate is literally a home w/in a home. The addition was built around the original log cabin. Wind Hill Farm is a 78 acre working equestrian facility, schedule a riding lesson on property. Local attractions: apple orchards, NH Speedway, wedding venues, Lakes Region, Gunstock Mountain.

4.95 out of 5 average rating, 108 reviews

Guest favorite

The exterior of a single-level home is framed by a gravel path and lush greenery, featuring a welcoming front deck. A cozy living space is highlighted by a grey sectional couch, a coffee table, and softly filtered light from a lamp. A large 86-inch TV showcases streaming options, while a dining area is furnished with a wooden table and matching chairs.

Home in Barnstead

Charming Lake Comm Bungalow - EV charging/86” tv

Welcome to our 3bd, 1ba cozy home in Barnstead, NH, just a 5 min walk to Locke Lake beach! Nestled amidst serene surroundings with access to 9 beaches on 2 lakes and pools, this charming retreat offers the perfect blend of rustic charm and modern amenities. Relax in style in our beautifully furnished living space, complete with an 86-inch TV, perfect for movie nights or catching the big game. With comfortable accommodations, area amenities and space for family and friends, your getaway awaits!

4.91 out of 5 average rating, 58 reviews

Top guest favorite

A charming red farmstead is set against a snowy landscape, showcasing a classic sloped roof and warm lights glowing from its windows. A fenced yard and a snow-covered driveway lead to the entrance, while snow-dusted trees surround the property.

Farm stay in Epsom

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

4.97 out of 5 average rating, 138 reviews

Guest favorite

A family lake house is positioned over the water, surrounded by lush trees. The two-story structure features multiple decks, providing space for outdoor activities. Colorful kayaks and paddleboards are visible along the dock, reflecting a peaceful lakeside ambiance under a partly cloudy sky.

Cottage in Alton

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay

Family lake house built over the water on Lake Winnipesaukee. Great place for families and children. Only 9 min. to Gunstock Mountain for exceptional NH skiing. Close to many amazing hikes and set in the middle of world class foliage! Quiet, serene, and restful cottage that offers something for everyone. Whether is swimming, paddle boarding, and hiking in the summer or skiing, ice fishing and relaxing by the wood stove in the winter, this cottage will relax and revive you and your loved ones.

4.94 out of 5 average rating, 85 reviews

Top guest favorite

Home in Barnstead

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.

4.98 out of 5 average rating, 42 reviews

Top guest favorite

Cabin in Barnstead

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).

4.95 out of 5 average rating, 272 reviews

Top guest favorite

Apartment in Pittsfield

Eaton Pond Retreat

Nestled on Catamount Mountain, this peaceful mountain retreat offers the perfect blend of relaxation and outdoor adventure. Enjoy scenic views from the gazebo, unwind by the firepit, take a dip in the pool, or launch a kayak right from the property’s pond. Surrounded by hiking trails, nearby lakes, and classic New Hampshire beauty, it’s the perfect escape year-round. Plenty of parking for trailers (boats and Snowmobile). Plenty of parking. message me if you have any questions.

5.0 out of 5 average rating, 23 reviews

Top guest favorite

A scenic view showcases a tranquil waterfront area featuring a new aluminum dock extending into Locke Lake. Colorful kayaks are positioned on the grassy shore, while a spacious deck is surrounded by outdoor seating arrangements. The calm water reflects the lush greenery of the surroundings.

Home in Barnstead

Lucky Duck Lodge - Waterfront home on Locke Lake

Welcome to Lucky Duck Lodge—a newly remodeled lakefront home perfect for family and friends. Enjoy all the fun of NH’s big lakes in a cozy, laid-back setting. Guests have access to 1 canoe, 8 kayaks (2 tandem), 2 paddle boards, a floating Otter Island, and a new aluminum dock. Two fire pits—one on the upper deck and one lakeside—make evenings magical. It’s the ideal spot for paddling, relaxing, and making memories.

5.0 out of 5 average rating, 71 reviews

Top guest favorite

An open living area features a grey sectional sofa paired with a wooden coffee table, centered on a light area rug. A wall-mounted television sits above a dark console. Brightness is enhanced by large windows with shades, while a dining area with white chairs is visible.

Home in Barnstead

Cozy modern Locke Lake getaway

Looking for a vacation spot in NH? Enjoy this quiet and charming Locke Lake home with tons of amenities. Perfectly located in the middle of the Lakes Region. After a day of fun, treat yourself to a soak in a beautiful spa tub. Enjoy your morning coffee or snuggle up to a good book on the large back deck. *25 Min to Gunstock Mt * 10 min walk to Locke Lake *15 Min to Winnipesaukee

5.0 out of 5 average rating, 36 reviews

Top guest favorite

A comfortable sitting area features two armchairs and a small coffee table on a patterned rug. Natural light enters through a window and an open door, revealing a view of the outdoor landscape. Wooden beams complement the warm, inviting aesthetic.

Guesthouse in Loudon

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.

4.98 out of 5 average rating, 387 reviews