Holiday rentals with a fire pit in Wolfeboro

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 Hobbit House w/ private hot tub

Fern Hollow 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.

Aspen Cottage - Charming Cottage with Beach Access

Nestled in the trees, at the end of a quiet road, you’ll find your next restful getaway. Central location perfect for relaxing or adventuring. Less than a 10 minute walk to multiple points of beach access or sunset viewing at Lower Beech Pond, a 155-acre lake within the Ossipee Mountain range, known for its excellent water quality and recreation. A 15 minute drive to downtown Wolfeboro and Lake Winnipesaukee. In the winter months, find miles of snowmobiling through NH's extensive trail system.

The Vineyard Penthouse - Beautiful Inside & Out

Wake up to rows of sun-kissed grapevines and unwind in a serene, vineyard-view retreat. This open-concept suite featured a plush king bed, abundant natural light and inviting modern décor. Sip wine at sunset, cook in the well-equipped kitchen, or unwind and relax, in our new “shared” hot tub. Although there are other guest on the property you will have this space to call your own and enjoy. ~ 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 20 min to Gunstock and 25 min to Bank of Pavilion

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.

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

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.

Waterfront w Kayaks, Pool table, Pergola, Firepit

Waterfront location nestled in the heart of Laconia. Located on a river connected to Lake Opechee.. Less than 5 minute walk the lake, beaches and downtown. A beautiful 7 mile walking trail “wow trail” right near the property. 2 water facing decks, 1 front porch, 2 grills, fire pit under the pergola, Sundeck on the river, and 2 kayaks are provided with the home. Close to lake Winni, Weirs beach, Bank of NH Pavilion, Gunstock ski and many more local attractions all 10 minutes away

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.