Waterfront holiday rentals in Milton

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.

River · Beach · Wi-Fi

Blue Breeze - Private lakefront w/ Hot Tub

This huge lakeside house is a great experience for all of your friends and family to enjoy all the New Hampshire lakes region has to offer. There is incredible nature all around! Some of our favorites nearby: 11min to a nearby brewery 12min to a great breakfast spot 14min to a farm stand and pick-your-own produce 17min to a nearby winery 21min to Hannafords grocery store 22min to Alton Bay 25min to Wolfeboro 29min to Mt. Major with views of Winnipesaukee 38min to Gunstock mountain for skiing

View · Beach · Decor

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

View · Beach · Laundry

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

View · Cleanliness · Family

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

This romantic & family-friendly lakefront chalet comes with a private beach, hot tub, kayaks & stunning views and is packed with amenities. It’s a serene home base to explore some of the best New England towns and is in the heart of the Lakes Region. Swim, kayak, bike a scenic trail, fish, hike, explore historic towns, farms & food scene, or simply grill with a view & play board games. We have poured our heart into making this a romantic yet very kid-friendly retreat (kids gear included).

Beach · View · Bathroom

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

River · View · Heating

Peaceful Glamping on private Beaver pond

We are offering a beautiful, COMFORTABLE, option to camping. Our off grid tent comes with all the comforts of home including a wood stove and reading nook! It is nestled into a hemlock grove overlooking the active beaver pond. Walking trails and local activities at a stones throw. If you have a small boat or kayaks- BRING them! We have space in the yard and lots of local places to send you to get good use out of them. Please do not use on our pond. We have a boat available for use.

View · Checkout · Access

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.

View · Beach · Bathroom

☀ 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!

View · Sleep quality · Quiet

Lovely Waterfront Seacoast Suite

Cozy waterfront suite , king size bedroom perfect for a relaxing escape. Just minutes from Portsmouth and Durham, it’s ideal for a romantic getaway, attending a local event, or visiting the University of New Hampshire. Enjoy a private patio and waterfront deck featuring a seasonally heated dome and a year-round fire pit. A duraflame log for winter use in the living room fireplace. You’ll find many nice extras here. Peaceful coastal charm near the New Hampshire–Maine border.

River · Beach · Access

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.

Beach · View · Hiking

Waterfront, Wood stove & Private beach, Solo Stove

Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

View · Beach · Indoor spaces