Holiday rentals in Shapleigh Pond

4.98 out of 5 average rating, 240 reviews

Farm stay in Alton

Mountain View - Modern & Beautiful

Kick back and relax in this stylish apartment space, with its own entrance around the back of the home! Modern construction w/ a king bed, large outdoor patio space w/ mountain views. A well-equipped kitchen/dining/living room combination that is great for short term or long term stays. Although there are other guest on the property you will have a private space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

4.9 out of 5 average rating, 520 reviews

Treehouse in Sanford

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.

4.93 out of 5 average rating, 14 reviews

Home in Newfield

Whispering Pines, Shapleigh Pond

Are you looking for the perfect place to get away from it all and make cherished memories with the people you love? This cabin, nestled in the beauty Vacationland has to offer, is perfect for you! Relax with the whole family at this peaceful retreat! Located on a secluded pond in Northwest York County, this cabin offers a variety of ways to enjoy the natural beauty that surrounds it. The cabin offers indoor and outdoor seating areas with views of the pond and treelined shore. Pet fee applies.

4.97 out of 5 average rating, 252 reviews

Cabin in Wakefield

Beautiful Log Cabin on Belleau Lake -2900 sqft!

Nestled among pine trees & views of the lake, the log cabin is the epitome of R&R. It is family/dog-friendly with an open concept main floor; 3 levels of living space (2900 sq ft). Perfect spot for large families looking to share a vacation without compromising privacy, while also perfect for a getaway for 2! Short walk to the beach, kayaks, fire pit, huge backyard & more! With year-round activities for the whole family, it's the perfect place to create lasting memories! 10% OFF WEEKLY STAYS!

4.99 out of 5 average rating, 135 reviews

Cottage in Acton

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake. Swing in the hammock while listening to the cry of the loons. Or enjoy your morning coffee overlooking the quiet cove from your covered porch. 100 feet of shoreline in the calm 3rd basin of the lake. This entire basin is a "no-wake" zone which allows safe swimming for the whole family. Enjoy fishing, search for turtles, or explore beyond the cove using the canoe, kayaks, or paddle boards. Dock your own boat at the 24' aluminum dock.

4.87 out of 5 average rating, 383 reviews

Flat in Porter

The Carriage House Apartment

A unique and inviting second floor apartment. Located in what was originally a carriage repair shop. Renovated into living space, the apartment offers a comfortable living room with high ceilings and exposed beams. A well equipped kitchen area, bedroom with two double beds and full bathroom. Our beautiful area offers a variety of activities including a scenic town beach a short walk down the road, hiking trails for all level, antique shops, great restaurants, seasonal fairs, and orchards.

4.99 out of 5 average rating, 93 reviews

Flat in Wakefield

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.

5 out of 5 average rating, 112 reviews

Guest house in Hiram

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

5 out of 5 average rating, 38 reviews

Guest house in Wakefield

Peaceful Spring Retreat: Private Horse Farm

Gorgeous views from the big bay window. A nice 1 mile walking trail. A full kitchen to make homemade meals. A large TV to settle in and relax. A workspace if needed. Laundry. Extra space could be used for storage/air mattress/kid space. Come experience farm life and let us know if you want a visit with any of the animals. Horses, chickens & dogs. Our place is a perfect getaway for a couple or small family. Escape the busy city noise. Relax at our firepit and check out the stars

5 out of 5 average rating, 204 reviews

Cabin in South Berwick

Romantic A-Frame cabin in the woods

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.

4.99 out of 5 average rating, 428 reviews

Home in Hollis

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

5 out of 5 average rating, 103 reviews

Home in Bridgton

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

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Other great holiday rentals in Shapleigh Pond

4.86 out of 5 average rating, 44 reviews

Home in Effingham

Direct Lakefront. Swim/Fish/Kayak White Mountains

LynneRating, 5 stars4 months ago

We enjoyed our stay in the cute cabin. Since it was winter and we were mostly away from the cabin visiting family, we didn't get to take advantage of the lake and activities. But we enjoyed sipping coffee at the kitchen table and taking in the view of the frozen lake.

4.86 out of 5 average rating, 94 reviews

Home in Freedom

Cozy camp for swimming, water sports and more!

BeckyRating, 5 stars3 weeks ago

The Pancake House was the perfect getaway! Peaceful, relaxing, comfortable, and charming! The house is better than the photos can show, and offered plenty of space for fun and relaxation. We enjoy evenings by the fire after enjoying the sunset on the lake!

4.95 out of 5 average rating, 19 reviews

Home in Shapleigh

Private Lake House with Docks & Views for Days

Jennie RyanRating, 5 stars8 months ago

Fantastic spot. We stayed in the fall. It was quiet on the lake. We enjoyed SUPing and Kayaking. Was happy to find “one earth” natural grocer up the road a bit. We enjoyed a fire in the wood stove every night. The Loons were a special treat too. It is steep and lots of stairs to the water but worth the climb. :) Lea was so accommodating and responded immediately to every inquiry. Hoping to book again next fall!

Holiday home in Parsonsfield

4.88 out of 5 average rating, 34 reviews

Randall Lake Retreat private lake 3 bdrm, 1 bath

AllyRating, 5 stars1 month ago

Great fishing spot for bass and pickerel. Quiet place, one of maybe 10 houses surrounding the pond. The property has kayaks and a canoe which we enjoyed. Tons of beautiful nature - we saw a bald eagle swoop right over us at sunset and heard frog mating calls throughout the night. The gazebo was also very useful for when it rained. Only issue we had was that the shower didn’t get hot - a little unexpected, but not the end of the world! Would absolutely book again.

4.98 out of 5 average rating, 59 reviews

Cabin in Wakefield

COZY CABIN | on Balch Lake, Pool table, Arcade

BrianRating, 5 stars2 weeks ago

Great place, we spent time relaxing on the screened in porch, very quiet and spacious, the kids loved it, we loved the downstairs space with the arcade, and did some hiking nearby and visited an alpaca farm close by and enjoyed the lake

4.94 out of 5 average rating, 36 reviews

Tiny home in Woodstock

Luxury Tiny Home Getaway- IRIS Home

RachelRating, 5 stars1 week ago

This tiny home was so aesthetically pleasing, in a beautiful location, with great amenities like the hot tub! We thoroughly enjoyed our stay and would highly recommend. William was a great communicator.

4.66 out of 5 average rating, 172 reviews

Cottage in Shapleigh

Entire Cozy Lakeside Camp with Boats

AreinaRating, 5 stars7 months ago

Walking into Andi‘s fishing cabin felt like going to grandma‘s house! It was so cozy and nice for our quick three day weekend in Maine. Everything that has been written in previous reviews is true. Including the extensive VHS collection lol! The view is beautiful, the atmosphere is peaceful, and we were so happy to sleep in the sunroom and wake up to the view of the lake Pond water in front of us. Easily accessible from the main road, close to restaurants, gas stations, and other amenities, including the Hannaford grocery. My fellow found himself on the dock fishing multiple times during our stay he caught a few trout. My favorite part is the fire pit area with the café lights. I love staying in the woods and this cabin fit our needs perfectly. Andi was a responsive host and we are grateful for his communication. Very positive and friendly! Hope to stay with you again next year!