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

Farm stay in Alton

4.99 out of 5 average rating, 308 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

Guest suite in Strafford

4.87 out of 5 average rating, 263 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

Cottage in Northwood

4.91 out of 5 average rating, 217 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

Apartment in Concord

4.98 out of 5 average rating, 283 reviews

Sunny Side Up

Sunny 2nd floor apartment set up in the trees in downtown Concord. A half mile walk or drive to historic main street shops and food. Private off street parking Centrally located right off of interstate 93 & 89. Plenty of seasonal activities nearby: Mountain biking, Skiing/Snowboarding/Snow Shoeing, Loudon Raceway, Apple Picking, Leaf Peeping, Lakes, Rivers, Ponds, Hiking The Space: Private open concept apartment with full kitchen, 1 bedroom with attached full bathroom. Cozy gas fireplace.

Guest favorite

Cabin in Barnstead

4.95 out of 5 average rating, 173 reviews

Scenic Lakefront Chalet: Hot Tub, Kayaks & 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, 491 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.

Guest favorite

Guest suite in Andover

4.97 out of 5 average rating, 118 reviews

Guest Suite - Andover Village

Cozy, clean, comfortable and convenient to Proctor Academy's campus, Upper Valley and local Lakes Region attractions. You have a private keyed entrance to a one bedroom and one bath suite in a bungalow home with off street parking. Although attached to the primary home, you enter from your own covered patio and have the suite entirely to yourself. The bedroom has a queen bed, compact bathroom with shower and pleasant sitting area for two. A relaxing atmosphere with a morning coffee amenity!

Guest favorite

Guesthouse in Belmont

4.99 out of 5 average rating, 201 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

Guest suite in Deerfield

4.92 out of 5 average rating, 213 reviews

The Guest Suite at Echo Hill Farm

Come get away to Echo Hill Farm, a traditional New England-style farm built in 1782. With a private entrance into the guest suite you can come and go as you please during your stay. Relax in the living room with a cup of coffee, while you watch fish jump in the pond behind the house. Centrally located, the mountains, the lakes region or the ocean are only an hour away from this quiet locale. There's even a farm-based Brewery 0.5 miles down the road with Pleasant Lake only 2.5 miles.

Guest favorite

Cottage in Gilmanton

4.97 out of 5 average rating, 204 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

Home in Northwood

4.99 out of 5 average rating, 116 reviews

Pleasant Lake Paradise - Heaven w/private hot tub!

Hot tub open year round! Don't see your dates available? Message me. We love our home away from home...with lake views, two bedrooms, 1.5 baths, and an expansive back deck with hot tub - our peaceful home on Pleasant Lake is sure to please. Boat, swim, kayak, hike, ice fish...or simply relax. In all seasons, this charming home has it all. And, we love your 4 legged friend! Dogs (only) welcome. Looking to rebook? PM sooner than later as I'm happy to accommodate repeat guests.

Guest favorite

Guest suite in Loudon

4.94 out of 5 average rating, 210 reviews

Private In-Law Apartment With Views and Hot Tub

NEWLY RENOVATED SEPTEMBER 2023! Private 1bed, 1 bath in-law apartment with dedicated entrance and no shared spaces, moments from historic downtown Concord NH. Sleeps up to 3 with queen bed and futon. Enjoy the sunset behind Mt. Kearsage while sitting around the fire pit overlooking the surrounding valley. Under 40 minutes to Gunstock Mountain and Pats Peak, and less than one hour to Crotched and Ragged Mountain. 30 minutes to Lake Winnisquam and Lake Winnepesauke.