
Holiday rentals in Pittsfield
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Top-rated holiday rentals in Pittsfield
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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.

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.

Antq. Farm Ell-Private deck/views/trails/Dog yard!
This farmstead "ELL" has 1800's character, yet updated for modern day. WiFi & AC! We hope this space inspires. Orig. hand hewn beams, pine floors, woodstove & vntg. bath tub to warm you after a day skiing or family sliding down threw the fields. Mtn. bike or walk the trails. Prvt. deck w/grill, fenced yard, firepit & views. We are here all 4 seasons @ "Windy Ridge Inn" Nh snowmobile trails at your door! UNH, Dell Lea, Gunstock Mt, Laconia, Atlantic Ocean, NH lakes, ME Outlets. 90 min to Boston

Vineyard Terrace - Modern & Beautiful
Step into a secluded vineyard retreat where elegance, privacy and breathtaking scenery meet. This suite offers a king bed, modern comforts and a spacious patio pergola with sweeping vineyard and mountain views. A well-equipped kitchen, dining and living area create the perfect setting for romantic getaways or extended stays. Though other guests share the property, this space is entirely yours to enjoy. 5 min from Lake Winni, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

Locke Lake Ski & Swim
Completely renovated home with private beach and waterfront. The water drops off gently making it great for young children. Variety of rafts, beach toys, kayaks, paddle boards, pedal and row boat available for use. Great fishing in the summer, and ice fishing in the winter. Outdoor deck is wonderful for entertaining. Seasonal game room in garage with shuffleboard and more. Located about 15 mins south of Lake Winnipesaukee and 30 mins from Gunstock Mountain. *Linens and Towels now included!*

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.

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 5 year old daughter. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

The Concordian - Walk to White Park, Downtown, UNH
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 fully renovated bathroom (as of 12/1/24!), full kitchen, one bedroom, a living/dining room with a pullout mattress with topper, plus two walk-in closets. Additionally, we provide air conditioning, high-speed internet, and Netflix for guests. The space is professionally cleaned AND linens are professionally laundered!

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!

Family lake house with pvt beach, dock
Come experience the beauty and tranquility of our private family lake house, On Locke, the perfect getaway spot for any season. *Summer: Private beach & dock, plus community beach with swing set & pavilion just steps away. *Fall: Stay warm with a cozy fire pit & access to nearby wildlife trails. *Winter: Ice fish, snowmobile, or ski with water front view & trailer parking. Ample space for trailers year-round to enjoy the water front view no matter the season.t home.

A - Farmhouse Apartment on a Cattle Farm
The apartment has a full private kitchen with a dishwasher. Breakfast is not provided. There is a one-time pet cleaning fee. We allow pets, but if you plan to leave your pet unattended in the apartment, dogs and cats must stay in an appropriate crate. We reserve the right to enter the apartment if an unattended pet is noisy or is not in a crate. The bathroom tub's bubbling jets do not work.

Modern Central Stylish Minimalist Unit w/ Laundry
Enjoy this stylish space at this centrally located apartment right in downtown Concord, designed for you and your family to relax, and enjoy what New Hampshire has to offer. We designed this space to accommodate your everyday needs as well as please the eye. ✓ 2 Mins to downtown ✓ 5 Mins to hospital ✓ Things to do/eat close-by ✓ Free on-site parking ✓ Easily Accessible ✓ Private Entrance
Popular amenities for Pittsfield holiday rentals
Other great holiday rentals in Pittsfield

Hill Studio

Bow lake Northwood, NH ~ Apartment w/ Kitchenette

Contemporary Countryside Home, Minutes to Concord

Modern Lakefront Cabin: Rustic Charm Meets Luxury

Bow Lake Escape

Romantic New England Historic Schoolhouse c1866

Historic 2nd-Floor Retreat with Modern Comforts

Charming Lake Comm Bungalow - EV charging/86” tv
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Jersey City Holiday rentals
- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Squam Lake
- York Harbor Beach
- Weirs Beach
- Monadnock State Park
- Long Sands Beach
- Canobie Lake Park
- Jenness State Beach
- Rye North Beach
- North Hampton Beach
- Pats Peak Ski Area
- Dunegrass Golf Club
- Tenney Mountain Resort
- Funtown Splashtown USA
- Salisbury Beach State Reservation
- King Pine Ski Area
- Short Sands Beach
- Wentworth by the Sea Country Club
- Parsons Beach
- Bear Brook State Park
- White Lake State Park
- Waterville Valley Resort




