Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

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Guest favourite

Farm stay in Alton

4.97 out of 5 average rating, 165 reviews

Mountain View - Modern & Beautiful

Kick back and relax in this stylish apartment space, with its own entrance around the back of the home! Modern construction w/ a king bed, large outdoor patio space w/ mountain views. 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 a private 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

Sep. 19 – 26

$173 CAD per night

Guest favourite

Guest suite in Strafford

4.87 out of 5 average rating, 259 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.

Nov. 25 – Dec. 2

$148 CAD per night

Guest favourite

Cottage in Northwood

4.91 out of 5 average rating, 214 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.

Aug. 21 – 28

$255 CAD per night

Guest favourite

Loft in Barrington

4.96 out of 5 average rating, 490 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.

Nov. 22 – 29

$150 CAD per night

Guest favourite

Apartment in Concord

4.97 out of 5 average rating, 323 reviews

Private Getaway in Downtown Concord

A quiet and beautiful updated second-floor apartment steps away from downtown Concord. The apartment is attached to a historic 1800’s New Englander home and has a full bathroom, full kitchen, one bedroom, a living/dining room, plus two walk-in closets. The apartment has been fully updated and newly furnished to provide a cozy and welcoming environment. Additionally, we provide air conditioning, high-speed internet, and Netflix for guests. This space is professionally cleaned and sanitized.

Feb. 1 – 8

$226 CAD per night

Guest favourite

Guesthouse in Belmont

4.99 out of 5 average rating, 200 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.

Dec. 16 – 23

$189 CAD per night

Guest favourite

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.

Dec. 2 – 9

$215 CAD per night

Guest favourite

Home in Northwood

4.99 out of 5 average rating, 115 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.

Nov. 5 – 12

$672 CAD per night

Guest favourite

Guest suite in Loudon

4.94 out of 5 average rating, 198 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.

Mar. 1 – 8

$196 CAD per night

Superhost

Condo in Tilton

4.81 out of 5 average rating, 197 reviews

Adventure Awaits

Newly updated and tastefully decorated cozy 1 bedroom condo unit with lake front views. Minutes away from popular local beaches and Lake Winnisquam marina. Enjoy all the outdoors has to offer at this year round getaway. Adventure awaits at Gunstock Mountain, Ragged Mountain, Bartlett Beach and Opechee Park. You can check out the local hiking trails, breweries and wineries, and so much more.

Sep. 30 – Oct. 7

$154 CAD per night

Guest favourite

Guesthouse in Loudon

4.97 out of 5 average rating, 237 reviews

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.

Sep. 24 – Oct. 1

$183 CAD per night

Guest favourite

Cottage in Epsom

4.97 out of 5 average rating, 188 reviews

Smokey Pines Camp

Cozy, private cottage on the Suncook river. Great for kayaking, fishing, tubing and swimming. Very private with meadow, outdoor picnic areas and fire pits. Within walking distance to Bear Brook state park. 40 minute drive to Portsmouth, Manchester, lake Winnepasakee. One hour away from New Hampshire White Mountains and Boston.

Sep. 26 – Oct. 3

$349 CAD per night