Vacation rentals in Pittsfield

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Lebanon

4.99 out of 5 average rating, 134 reviews

Rustic Rose Cottage of Historic West Lebanon

Rustic guest suite on serene four acres. Abutting colonial cape style house and West Lebanon Historic District date back to early 18th Century. Private parking & entrance, queen memory foam mattress, steam sauna, kitchen and laundry supplies, and desk and high speed wifi for telework. Minutes from Skydive New England, Prospect Hill Winery or McDougal Orchard. 30min to Portsmouth NH, Maine beaches, and Lake Winnipesaukee. Just over an hour to the White Mountains, Portland ME or the Boston area.

Guest favorite

Guest suite in Strafford

4.88 out of 5 average rating, 283 reviews

The West Wing: A perfect romantic getaway

The perfect romantic get away / launch pad for local events. 2 private rooms, main bedroom, sitting room / bedroom, with full size sofa bed. Plus full bathroom, dual vanity & kitchenette. Enjoy a private deck, entry doors and parking steps away. Beautiful foliage in season, nearby lakes, state parks, snow shoeing, x country & down hill skiing. 15 minutes to UNH & 25 minutes to the seacoast. Located on a "scenic" road. Wonderful for long walks while you take in the beauty of New Hampshire.

Guest favorite

Farm stay in Alton

4.99 out of 5 average rating, 365 reviews

Treehouse Penthouse ❤ Beautiful inside & out

Kick back and relax in this calm, stylish apartment space. This space is an open concept with a king size bed. Lots of windows bring in natural light, cathedral ceiling and amazing view! A well-equipped kitchen/dining/living room combination that is great for short term or long term stays. Although there are other guest on the property you will have your own space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

Guest favorite

Cottage in Northwood

4.91 out of 5 average rating, 252 reviews

Cottage near lake! Includes canoe! Dog friendly!

Come relax, sit by the fire pit, walk the dirt roads & trials! Walk 2 min. to the boat launch/swim area & enjoy the canoe. WIFI. 500 mbps. Yard: grill out, make s'mores by the fire pit, play horse shoes. Inside: play games, complete puzzles, cuddle up and watch movies. Outings: Antique Alley, Chucksters, Stonehouse Pond, Meadows State Park, Portsmouth,Concord. *Sleeps 4. *PET FEE $25 per dog/ night. 1-2 behaved dogs. Dogs only due to health concern for cleaner. *Wear life jackets provided.

Guest favorite

Cabin in Barnstead

4.95 out of 5 average rating, 197 reviews

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

This romantic & family friendly lakefront chalet comes with a private beach, hot tub, camp fire, and stunning views. It’s a serene home base to explore everything the Lakes Region has to offer. Mid Apr-Oct we also provide kayaks and paddle board. Enjoy the beach, swim, kayak, bike, fish, hike, or explore quintessential New England towns and food scene. Or simply dine with a view and play board games. We have poured our hearts into making this place romantic yet practical for families. Enjoy!

Guest favorite

Loft in Barrington

4.96 out of 5 average rating, 521 reviews

Sunny, secluded studio loft apartment

Fully furnished studio apartment above home owners' garage with private entrance. Secluded 5.5 acre lot of land surrounded by beautiful woods. Vaulted ceilings with ladder to loft with queen bed. Big, sunny south-facing windows overlooking back yard and gardens. Homeowners are a laid-back, married gay couple, living in the main house with their 2 year old daughter and a dog. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

Superhost

Tiny home in Gilmanton

4.78 out of 5 average rating, 243 reviews

Tiny Home with Tiny Cows on a Working Farm!

You'll love this unique escape! Stay in your own tiny home complete with a roof top deck, sky light & fire pit-- in the middle of a field located at a historic farm in the Lakes Region of NH! You'll find peace amongst the horses, potbelly pigs, mini cows listening to the occasional rooster- surrounded by a field & trees. Located in the historic area of Gilmanton- Close to Gunstock ski area, Bank of NH Pavilion, restaurants, Lake Winni (along with many other ponds & lakes) & endless hiking!

Superhost

Cabin in Epsom

4.84 out of 5 average rating, 653 reviews

Postcard Cabins Blake Brook - Boston

An easy drive from the city, Postcard Cabins, formerly Getaway, is the ultimate way to experience the great outdoors. Nestled across acres of private woodlands, our tiny cabins have everything you need (AC/Heat, en-suite bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you disconnect from the everyday. As part of your stay, you'll receive a complimentary allocation of provisions, like s’mores, coffee and more.*

Guest favorite

Home in Lebanon

4.96 out of 5 average rating, 209 reviews

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Guest favorite

Guesthouse in Belmont

4.98 out of 5 average rating, 223 reviews

Charming Pool/Garden Guest House

A little Paradise! Charming pool and guesthouse in country setting, birds and flowers galore. Much to do in the area, or just quiet, settling into some refresh-your-soul time. The guesthouse has all you need to feel at home. Within 15 minutes you'll find Gunstock Recreational Area, Highlands Mtn. Bike Park, Hermit Woods Winery, Funspot bowling and arcades, hiking, fishing, Shaker Village, Lakes Region Casino, NH Speedway, Bank of America Pavillion (concerts) and Tanger Outlet Shopping.

Guest favorite

Cottage in Gilmanton

4.96 out of 5 average rating, 227 reviews

Cozy Cottage Near Crystal Lake

Cozy guest cottage tucked away in the quiet town of Gilmanton. On a small hill with just a short walk down to Crystal Lake to launch your kayak or take a dip. This adorable year round camp has many necessities and is the perfect place to unwind. Less than a mile to the local beach and boat launch. Only 15 minutes to Alton Bay & Lake Winnipesaukee, and close to Gunstock Mt., Tilton shopping & restaurants and the Weirs. Come enjoy the mountains and lakes in the beautiful Lakes Region!

Guest favorite

Guest suite in Canterbury

4.91 out of 5 average rating, 133 reviews

Cozy Canterbury Suite

Discover the perfect retreat in Canterbury, NH! Our 1 bed, 1 bath unit is a cozy haven, centrally located for lakes and mountain adventures. Spanning 850 sq ft, it offers comfort with a queen size bed and a pull-out couch to sleep a total of 4. Nestled by snowmobile trails, minutes from Highland Mountain Bike Park, Canterbury country club, and the historic Shaker Village. Unwind in nature's embrace, where every season paints a breathtaking canvas. Your ideal getaway awaits!