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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.

The Ladd House
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath
The Ladd HouseClear your mind and relax. That's the sort of atmosphere the Ladd house has to offer. Built in the 1700's by Daniel Ladd this grand old house has plenty of charm, open land, gardens and a secluded pond for you to explore. Quite an assortment of song birds frequent the bird feeders for your viewing.
Tranquil getaway w Hottub, game room & relaxation
SUPERHOST
Entire residential home · 14 guests · 8 beds · 2 baths
Tranquil getaway w Hottub, game room & relaxationIf you’re looking for peace and tranquility, this is the place. Our unique home offers a relaxing & private country setting. A fun getaway w friends & family, or just to be romantic . Our new 8 person large salt water hottub adds some much needed relaxing time on a roof top deck. Game room & pool table fun too. Gunstock Mountain, Winnipesaukee, Alton Bay are great for day trips. Barnstead has many year round activities such as snowmobiling, hiking, fishing, kayaking, canoeing and lake access.
Winter Retreat New England Cape/Equine Drake House
SUPERHOST
Farm stay · 4 guests · 2 beds · 1.5 baths
Winter Retreat New England Cape/Equine Drake HouseNEW ENGLAND DESTINATION! Charming 9 acre historic home adjacent to 100+ acres of trails, rivers, apple orchards and horse pastures. Rustic setting, built in 1775 and updated in 2019. Bee Hive ovens, hardwood floors, exposed beams, all from 1700's. Beautiful country setting, vistas across Catamount Range, end of a private road. Natural privacy in a lovely setting, local restaurants and amenities, this is the place! Horse boarding and paddocks also available for equine enthusiasts

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Other great vacation rentals in Pittsfield

SUPERHOST
  1. Farm stay
  2. Loudon
Unique Equine Estate w/an Indoor Pool & Hot Tub.
$650 per night
  1. Entire residential home
  2. Barnstead
Dog-Friendly Home on 1/4 Acre with Deck, Firepit, Electric Fireplace & Free WiFi
$213 per night
SUPERHOST
  1. Entire cabin
  2. Barnstead
NEW Modern Lake & Ski Chalet w/ Breathtaking Views
$258 per night
  1. Entire loft
  2. Epsom
Charming Loft on Lords
$95 per night
SUPERHOST
  1. Entire cottage
  2. Barnstead
Mountain Breeze Cottage +250 acres farm and forest
$348 per night
SUPERHOST
  1. Entire residential home
  2. Barnstead
NEW! Fam-friendly 4BR Waterfront Barnstead Beauty
$513 per night
SUPERHOST
  1. Entire residential home
  2. Barnstead
Enjoy river life in a family friendly farmhouse!
$400 per night
  1. Entire residential home
  2. Barnstead
Cozy A-Frame Center Barnstead House on Locke Lake!
$220 per night
  1. Entire residential home
  2. Barnstead
Pet-Friendly Home w/ Private Beach, Dock & Rafts!
$482 per night
SUPERHOST
  1. Private room
  2. Loudon
Louis L'Amour suite
$85 per night
SUPERHOST
  1. Entire guesthouse
  2. Loudon
Pastoral Farm in NH
$85 per night
SUPERHOST
  1. Entire guesthouse
  2. Barnstead
Lakefront Carriage House
$100 per night