Holiday rentals with outdoor seating in Wolfeboro

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!

Lake Access + Kayaks+Arcade+Bike Path+Private deck

Welcome to the Striped Loon! Our newly updated 2bd/1ba cottage is just steps away from Crescent Lake (great for kayaking) and Cotton Valley Rail-trail walking/bike path leading directly into downtown. Perfect for families , small friend groups, or couples our home offers the below amenities to enhance your stay! -Beach pass & towels, chairs, blanket -Two player arcade, Board games, pickleball set -TV for streaming -Private deck with grill, dining area and deck fire pit -Kayaks, lifejackets

Luxury Year-round Treehouse with private hot tub

The Canopy 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.

Caretakers Apartment-Split level w/ Wet Room Bath

Caretaker's Studio Apartment on the back of the Main House with a separate entrance. Enter on the first floor into a small living room with two chairs and Bathroom, climb 12 stairs up to kitchen/bedroom. The kitchen includes a sink, cabinets for storage, stove/oven combo and refrigerator open to the bedroom which includes a Double Bed is under the Elevated Loft with a Single Bed that is suitable for a child. The space is private and fully sound insulated. Guests can enjoy all of the common area

Pretty & Peaceful….close to Lake Winni!

Welcome to your Alton Bay retreat! Come relax & make lasting memories. Very clean, well stocked full kitchen & bath. Across the street is 200 acres of picturesque hiking trails & fishing. Turn left at the end of driveway and enjoy a scenic walk along Winni. Quiet location but close enough to Lake Winnipesaukee, Mt Major, Wolfeboro, Bank of Pavillion, boat launches, & docks, beaches, restaurants, shopping, sking, snowmobiling, boat rides, scuba diving, biking, kayaking, leaf peeping!

Luxury Beachfront Cottage - Perfect summer getaway

A private lakeside sanctuary for two on pristine Lake Wentworth, minutes from Wolfeboro. Set on six secluded waterfront acres of thoughtfully tended gardens and woodland, this refined cottage offers rare quiet and natural beauty. Wake to loons, kayak glassy morning water, ride complimentary beach cruisers to town, wander native pollinator gardens, and share long sunsets by the beach firepit. Evenings end wrapped in hand-pressed luxury linens. Calm, intimate, restorative. Reserve your stay.

Lake Winnie Cozy Cottage Getaway

Welcome to Lake a Dream… your spot for a fun filled family vaca on Lake Winnie in the summer or a cozy couples getaway in the winter! With just a quick 3 minute walk from the property you can enjoy some sunshine & sand on the beach! Or a 5 minute drive into downtown Wolfeboro to experience it’s charm; waterfront dining, ice cream, shops, cafés & more! For winter stays, cozy up by the fireplace with a cup of hot cocoa & some fun family games! The cottage is not far from Gunstock & Kingpine!

Peaceful getaway with King Bed near Town

Welcome to the perfect Wolfeboro Getaway! King size memory foam mattress for a rejuvenating nights sleep. You will love the peace and quiet of this location with easy walkable access to everything in downtown Wolfeboro, Back Bay, and the waterfront. For nature lovers, there's hiking trails right at the end of the street, just take a left out the front door. Please note: There is a kitchenette with sink, refrigerator, coffee maker, toaster oven, and plug in cook top but no actual stove.

Maple Hill Cottage Suite

Come and enjoy a relaxing stay at Maple Hill Cottage suite and experience New England seasons and all they have to offer, 5 minutes from Lake Winnipesaukee and downtown Wolfeboro, 3 minutes to Abenaki Ski Area and 30 minutes from Gunstock Ski Resort. Nestled amongst Sugar Maples on 13 acres attached to the host's home with separate private entrance. You are sure to enjoy a cozy retreat. Apartment boasts King size bed, custom kitchen with washer/dryer, full bath and fast internet.

Downtown Wolfeboro condo on Winnipesaukee w/Dock!

It's one thing to be right downtown in beautiful Wolfeboro, but add being right on the water w/your own porch, as you look over Wolfeboro Bay. Always something beautiful in front of you. This was my personal unit for a couple of years. It's fully equipped with a brand new bathroom lrg. tile shower, full kitchen, 55" UHD TV, Hi-Speed Internet, new Split System AC is comfy & quiet & a lrg. sectional couch that'll sleep-2 very comfortably. Lake living at its finest.

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

King’s Cottage PERFECTLY LOCATED!

The Cottage offers the perfect getaway for couples or small family. First floor living with 2 additional bedrooms upstairs, plus tween/teen lounge area & kids corner. The cottage is on a quiet street, but walkable to coffee, restaurants, and downtown shopping. Great proximity to Lake Winni, Sewall Woods, Cottonwood Rail Trail. It's an easy 1 hr drive from Manchester airport or 2 hr from Boston.