
Holiday rentals in Pleasant Lake
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Top-rated holiday rentals in Pleasant Lake
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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.
5.0 out of 5 average rating, 325 reviews
Waterfront Cottage Private Dock | 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.
4.94 out of 5 average rating, 162 reviews
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.
4.92 out of 5 average rating, 132 reviews
Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.
4.99 out of 5 average rating, 179 reviews
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
4.97 out of 5 average rating, 139 reviews
Lakeside Cottage with Private Dock, Canoe
Escape to this charming, lakeside cottage on beautiful Pleasant Lake - one of New Hampshire’s cleanest and clearest. Enjoy breathtaking views, cozy air-conditioned interiors, and direct access to swimming, fishing, and boating. Relax on your private dock, or bring your boat, PWC, and other water toys. Explore the lake in the 14ft canoe. Perfect for couples, families, or friends seeking a peaceful retreat in nature’s embrace. Book now for an unforgettable experience on beautiful Pleasant Lake!
5.0 out of 5 average rating, 43 reviews
Perfection on Pleasant Lake
Message me if you don't see dates you need -we block time for ourselves. Relax and enjoy this air conditioned comfortable and modern lakeside house. Swim, kayak, canoe, paddle board or lounge on our spacious dock where you can dock your boat as well. Gorgeous gardens, two large decks, fire pit area. Large Primary Suite with King bed and pull out bed. Newly renovated, stocked kitchen, Dining table for 8, fast Wi-Fi, house stocked with puzzles, books games. Up to 2 dogs welcome.
5.0 out of 5 average rating, 42 reviews
The Loon Nest, Waterfront Lake House, Wood Hot Tub
Welcome to The Loon Nest! Recently updated Waterfront lake House Retreat w/ Sleeping for 8. Bring your well behaved dog and enjoy being directly on the water with a 20ft dock for all your aquatic adventures. Private community beach is right next door with Picnic tables and swimming platform. The house Features 3 bedrooms, 1 bath, full kitchen, screened in porch, and also has a wood fired cedar hot tub! Come enjoy the very quiet 100 acre pond and experience an awesome getaway.
4.97 out of 5 average rating, 125 reviews
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.
4.97 out of 5 average rating, 192 reviews
Lakefront House on Pleasant Lake - Pet Friendly
This is the perfect vacation spot for year round adventure. Steps away from one of the top clearest lakes in NH. Sandy shore is the dream vacation whether you’re looking to kick back and relax, do water sports, swim, boat, kayak with the loons, ice skate, cross country ski, snowmobile, fish or view the fall foliage. Bring your own boat and park it at the private dock or use our 2 person kayak equipped with oars and life jackets.
4.96 out of 5 average rating, 24 reviews
Drakes Island Beach Front Breathtaking Property !
Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !
4.88 out of 5 average rating, 144 reviews
Loon's Ledge Lakehouse
Escape to our charming lakeside retreat in the heart of Northwood, NH, where relaxing days and outdoor adventures await! Perfectly positioned with serene views of Northwood Lake and just a stone's throw from the excellent fishing, local breweries, restaurants and more, our 3-bedroom, 1 bathroom home (plus a fantastic private outdoor shower!) is the ideal getaway for families, couples, or friends.
5.0 out of 5 average rating, 28 reviewsPopular amenities for Pleasant Lake holiday rentals
Other great holiday rentals in Pleasant Lake

Deja Blue Lake House
5.0 out of 5 average rating, 31 reviews
Lake House & Beach, Pets Welcome
4.97 out of 5 average rating, 35 reviews
Vasha Lakehouse
5.0 out of 5 average rating, 27 reviews
Fall Foliage on the Lake Kayaks | Private Dock
4.96 out of 5 average rating, 67 reviews
Charming, Relaxing Northwood Cottage
4.93 out of 5 average rating, 28 reviews
Magical Milton in Fall | Cozy | Bonfire | Hot Tub*
5.0 out of 5 average rating, 3 reviews
Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay
4.94 out of 5 average rating, 87 reviews
Grapevine Cabin
4.92 out of 5 average rating, 100 reviewsDestinations to explore
- White Mountain National Forest
- Ogunquit Beach
- Hampton Beach
- Wells Beach
- Squam Lake
- Weirs Beach
- Long Sands Beach
- Short Sands Beach
- Canobie Lake Park
- Pats Peak Ski Area
- York Harbor Beach
- North Hampton Beach
- Cape Neddick Beach
- Footbridge Beach
- Monadnock State Park
- Crane Beach
- Snhu Arena
- Jenness Beach
- Hills Beach
- Gooch's Beach
- Fortunes Rocks Beach
- Salisbury Beach
- Tenney Mountain Resort
- Salem Witch Museum





