
Holiday houses in Pittsfield
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Top-rated holiday rentals in Pittsfield
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Cottage on the lake! Includes kayaks & rowboat!
Super cozy, beautiful cottage on the lake & dirt roads.Yard: sitting areas, propane fire pit & grill, fenced in yard.Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided.

Romantic A-Frame cabin in the woods
Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Peaceful Mill with Waterfall - Home Away From Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

Cozy A Frame Cabin
Discover Your Dream Getaway at Our Enchanting A-Frame Cabin in Danbury, NH! Hike lush forest trails, paddle across sparkling lakes, or hit the nearby slopes for seasonal adventure. After a day outdoors, kick back on the spacious deck, fire up the grill, and dine under the stars. Whether you're planning a romantic escape or a fun-filled family getaway, this hidden gem offers the perfect blend of comfort, charm, and natural beauty. Escape the ordinary—book your unforgettable Danbury retreat today!

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 open year round @ "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

Luxury Year-round Treehouse with private hot tub
Skyframe is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

The Barnstead Train Depot 1889
Romantic and cozy 1 bedroom home in Barnstead, New Hampshire. A former train depot built in 1889, this historic home stands on the banks of the Suncook River Reservoir. Enjoy private dock access for fishing, swimming, canoeing and kayaking. Immerse yourself in nature on a walk through the woods on the attached rail trail. Enjoy sunsets and river views directly from the deck. When the sun goes down be sure to stick around to view the blanket of stars that have blessed the Depot for 136 years.

Eaton Pond Retreat
Nestled on Catamount Mountain, this peaceful mountain retreat offers the perfect blend of relaxation and outdoor adventure. Enjoy scenic views from the gazebo, unwind by the firepit, take a dip in the pool, or launch a kayak right from the property’s pond. Surrounded by hiking trails, nearby lakes, and classic New Hampshire beauty, it’s the perfect escape year-round. Plenty of parking for trailers (boats and Snowmobile). Plenty of parking. message me if you have any questions.

Luxury Glamping NH - Geodome Sanctuary
Escape to a private luxury sanctuary retreat tucked behind a small family owned Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, hammock and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 80 minutes from Boston, yet a world away.

Riverway Cabin
Make some amazing memories at this unique and family-friendly cabin. Nestled amongst a quiet river front at Epsom Valley Campground, you have all the comforts of the cabin and all the fun of the campground. With a queen bed and twin bunk- this is great for small families or couples. Join for the activities or stay within your private site- you choose your stay! There are lots of great walking trails, shopping, and local restaurants and breweries nearby!

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.

Epsom Lakefrnt Escape~Dock~Grill~Firepit-Woodstove
🏡🌊 Welcome to Your Lakefront Retreat in Epsom, NH! Escape to this spacious lakefront home perfect for families, friends, or anyone looking for a peaceful getaway. With direct lake access 🛶, a private dock, grill 🍖, firepit 🔥, and cozy wood stove 🪵, this home combines relaxation, adventure, and comfort for a memorable vacation experience.
Popular amenities for Pittsfield holiday rentals
Other great holiday rentals in Pittsfield

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Loon's Ledge Lakehouse

Charming Lake Comm Bungalow - EV charging/86” tv

Charming, Relaxing Northwood Cottage
Destinations to explore
- New York City Holiday rentals
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- Mont-Tremblant Holiday rentals
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- York County Holiday rentals
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- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Weirs Beach
- Long Sands Beach
- Pats Peak Ski Area
- York Harbor Beach
- Canobie Lake Park
- Short Sands Beach
- North Hampton Beach
- Monadnock State Park
- Footbridge Beach
- Cape Neddick Beach
- Tenney Mountain Resort
- Gooch's Beach
- Snhu Arena
- King Pine Ski Area
- Salisbury Beach
- Jenness Beach
- Gunstock Mountain Resort
- Ragged Mountain Resort
- Hills Beach
- Waterville Valley Resort





