Vacation rentals in Middleton

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.

Value · Location · Bathroom

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.

Location · Value · Accuracy

Mountainside Chalet+Sauna Near Gunstock Ski Resort

Enjoy everything Lake Winnipesaukee and the White mountains have to offer. Located directly between downtown Wolfeboro and Alton Bay, a short 10min drive will get you to either. A 30min drive will get you to Gunstock Resort or Mount Major. Enjoy gorgeous sunsets and views from the elevated deck, while you sit around a gas fireplace. The interior provides a spacious open concept layout with a large couch, 75" TV and a stocked kitchen. Enjoy the health benefits of the relaxing Infrared Sauna.

Location · Family · Condition

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Value · Location · Amenities

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.

Family · Value · Hospitality

Waterfront Chalk Pond | Fireplace | Kayaks

Birch Hill House on Chalk Pond is a bright waterfront retreat for every season. Cathedral ceilings and expansive windows frame glowing sunset water views while a cozy electric fireplace warms crisp evenings. Enjoy hiking, birding, kayaking, fishing, and swimming from the private beach, then unwind by the fire pit or relax on the spacious deck. Watch for loons and eagles and explore nearby Birch Ridge trails, Powder Mill snowmobile routes, and the Lakes Region. 90 minutes from Boston.

Location · Family · Comfort

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Location · Family · Beach

Cozy Lakes Region Escape. Fire Pit. Patio

Welcome to Buttercup Inn Tucked away in the peaceful lakes region, less than 2 miles from downtown Wakefield, this tastefully upgraded home may just surprise you. Every detail has been designed to make you feel right at home, from cozy furnishings to the brand new coffee bar- your go-to spot for a perfect brew. Whether you're unwinding or exploring the area, this charming retreat's proof that sometimes the best places are the ones you least expect. Message for further info.

Location · Family · Wifi

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting. The sunsets can be unbelievable!

Location · Family · Decor

Lake Living, sit back and relax!

This house will give you and your family a private place to hang out near the lake. The backyard is a serene beautiful place to hang out with family and friends. There is lake access right into the water. Paddle board and kayaks available for some water fun. 🛶 In addition there is a fire pit with seating, gazebo with seating and outdoor TV, grill, and a swing set for the kiddos. Beautiful water views from inside the house too. 🌅 Lots of bed space for multiple families.

Family · Location · Layout

Magical Milton in Fall | Cozy | Bonfire | Hot Tub*

Welcome to Camp Lollywood at Milton Three Ponds—a modern luxury lakefront retreat for unforgettable fall getaways. This sleek 3-bedroom, 2-bath lakehouse sleeps 8 and blends sophisticated design with genuine warmth. Step inside to clean lines, soaring ceilings, and a fireplace perfect for cozy evenings. The chef's kitchen and open living spaces flow to your private dock and sandy beach. Firepit nights, s'mores, and stargazing define your stay. Hot Tub Coming Fall 2026!

Location · Family · Bathroom

Hope's Haven-Lakefront House with Beautiful Views

Sunrise Lake is quiet, serene & pristine. The year-round panoramic views from our house are breathtaking! Dog friendly | Hot Tub | Kayaks | Paddle Boards Hope’s Haven is designed for you to enjoy the view! Watching the sunrise over the misty lake is magical. We are positioned for optimal sunrise views from the deck, lanai, living room and hot tub! After a blissful day enjoy cotton candy skies at sunset & sensational star-gazing at night.

Location · Family · Cleanliness