Holiday rentals in Pittsfield
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Pittsfield
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest suite in Strafford
4.87 out of 5 average rating, 259 reviewsThe 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.
17–24 Jun
Cottage in Northwood
4.91 out of 5 average rating, 214 reviewsCottage 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.
28 Sep – 5 Oct
Loft in Barrington
4.96 out of 5 average rating, 489 reviewsSunny, 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.
25 Aug – 1 Sep
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield holiday rentals
Other great holiday rentals in Pittsfield
Cottage in Middleton
4.96 out of 5 average rating, 135 reviews☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
18–25 Oct
Cabin in Barnstead
4.95 out of 5 average rating, 164 reviewsScenic Chalet: Hot Tub, Amazing Views, Near Skiing
5–12 Jun
Farm stay in Alton
4.99 out of 5 average rating, 298 reviewsTreehouse Penthouse ❤ Beautiful inside & out
19–26 Oct
Cottage in Alton
4.87 out of 5 average rating, 156 reviews1 Bedroom Cottage w/Lake Winnipesaukee View/Access
3–10 Feb
Flat in Newmarket
4.96 out of 5 average rating, 196 reviewsSpacious private Studio & Experienced SuperHosts!
29 Apr – 6 May
Farm stay in Epsom
5.0 out of 5 average rating, 70 reviewsAntq. Farm Ell-Private deck/views/trails/Dog yard!
8–15 Feb
Cottage in Barrington
4.92 out of 5 average rating, 49 reviewsA little house in the woods
15–22 Nov
Home in Epsom
4.96 out of 5 average rating, 51 reviewsWaterfront Getaway Home in Epsom, NH
19–26 Dec
Home in Pittsfield
5.0 out of 5 average rating, 21 reviewsRestored Historic Colonial with Mountain Views
10–17 Apr
Home in Epsom
4.98 out of 5 average rating, 63 reviewsLakefront-Dock-Grill-Firepit-Wood Stove
13–20 Oct
Guest house in Alton
5.0 out of 5 average rating, 7 reviewsRiver Run Cottage in Alton, NH
7–14 Sep
Flat in Alton
4.92 out of 5 average rating, 61 reviewsDowntown, Super Private & Cozy Loft Style Apt.
23–30 Aug
Destinations to explore
- Cambridge Holiday rentals
- Portland Holiday rentals
- Salem Holiday rentals
- Chebacco Lake Holiday rentals
- Old Orchard Beach Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
- Québec City Holiday rentals
- Québec Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom