Holiday rentals in Milton

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.

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.

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.

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.

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.

NH Lake House w/Private Beach, Hottub, & Lg Deck

Perfect for family or friend getaways. Privacy, luxury, and abundant amenities. - Formal open-concept living room & entertainment rooms - 120ft covered deck overlooking lake - Remodeled modern kitchen - Private beach (big enough for volleyball games!) - Walkout finished basement (with bar) - Tiki Bar on beach - 8-person outdoor hottub to watch sunsets - 50ft dock for large boat - Firepit, kayaks - Windows throughout house; every room has a terrific view of the water & sunsets.

Hot Tub | Lakeside | Private Beach | Sleeps 12

🛶 Lakeside with sandy beach & 4 Kayaks 🔥 Hot Tub for 6 people overlooking the lake 🛥️ Dock to boat, swim & fish - 750 acre lake! 🛋️ Living rooms on both main and lower levels ⚽ Big TVs and a Foosball table 🌲 3 minute walk to wooded walking trails 🍓 2 mins to McKenzie's Farm (farm stand, fruit picking, fresh apple cider donuts) ⛷️ 40 mins to Gunstock skiing 🛷 15 mins to Moose Mountain snow tubing 🦞 35 mins to Portsmouth, 65 mins to Portland 🏢 80 mins from Boston metro

☀ 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!

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.

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!

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.

Lovely cottage on Sunrise Lake, Middleton, NH.

A lovely lake-front cottage with a private beach on quaint Sunrise Lake! The house has a great view overlooking the water. Enjoy a beautiful morning view of the sun rising onto the lake with a cup of coffee or tea, grilling a tasty dinner on the deck, and toasting marshmallows in the fire pit for dessert. We also provide a double kayak so you can explore the mile-long lake from the easy launch point in front of the house.