Waterfront vacation rentals in Milton

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Top-rated waterfront rentals in Milton

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Top guest favorite

A cabin with a spacious deck overlooks a natural setting. The structure features large windows and a bright red umbrella set over a wooden table. Surrounding green trees and shrubs create a serene environment, while a canoe rests nearby on the ground.

Home in Wolfeboro

4.99 out of 5 average rating, 134 reviews

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

Top guest favorite

The open-concept living area features a sleek gray sofa with decorative pillows and a spacious wooden dining table. Natural light floods the room through large windows, while a wall-mounted TV enhances the entertainment options. The warm wooden ceiling adds a cozy touch.

Cottage in Wakefield

4.99 out of 5 average rating, 100 reviews

Gorgeous Romantic Lakefront Getaway

Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

Top guest favorite

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

4.9 out of 5 average rating, 540 reviews

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.

Top guest favorite

A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.

Home in Windham

4.94 out of 5 average rating, 163 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Guest favorite

An open concept living area is visible, featuring large floor-to-ceiling windows that provide a view of the serene lake and outdoor seating. A light wood dining table is set, accompanied by stylish chairs. A wood-burning stove stands in the corner, enhancing the space's warmth.

Cabin in Barnstead

4.95 out of 5 average rating, 240 reviews

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

This romantic & family friendly lakefront chalet comes with a private beach, hot tub, camp fire, and stunning views. It’s a serene home base to explore everything the Lakes Region has to offer. Mid Apr-Oct we also provide kayaks and paddle board. Enjoy the beach, swim, kayak, bike, fish, hike, or explore quintessential New England towns and food scene. Or simply dine with a view and play board games. We have poured our hearts into making this place romantic yet practical for families. Enjoy!

Top guest favorite

A cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.

Cottage in Middleton

4.97 out of 5 average rating, 162 reviews

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.

Top guest favorite

The welcoming entrance of a beachfront home features a porch with a blue umbrella and an American flag, surrounded by vibrant pink and green landscaping. A wooden staircase leads to the entry, providing easy access to the main living area.

Home in Rye

4.98 out of 5 average rating, 320 reviews

*Beachfront* Vintage Coastal Cottage - Relaxation

It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here: https://bit.ly/3vK5F0G We've outfitted it with an extra screen and a setup to get you up and running. Google home and Sonos systems bring this 100 year old beauty into this century.

Guest favorite

A wooden swing hangs from two trees, overlooking a serene lake. The vibrant greenery is visible in the background, along with a dock extending into the water. The scene captures the calmness of nature, enhanced by soft blue skies and gentle clouds.

Home in Barnstead

4.9 out of 5 average rating, 131 reviews

Family lake house with pvt beach, dock

Come experience the beauty and tranquility of our private family lake house, On Locke, the perfect getaway spot for any season. *Summer: Private beach & dock, plus community beach with swing set & pavilion just steps away. *Fall: Stay warm with a cozy fire pit & access to nearby wildlife trails. *Winter: Ice fish, snowmobile, or ski with water front view & trailer parking. Ample space for trailers year-round to enjoy the water front view no matter the season.t home.

Guest favorite

A modern cabin exterior is framed by tall trees, featuring a large window that invites light into the interior. A spacious wraparound deck is present, enhanced by warm, glowing string lights. Comfortable outdoor seating is arranged on the deck, creating an inviting atmosphere.

Home in Bridgton

4.98 out of 5 average rating, 133 reviews

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.

Guest favorite

A round dining table with two white chairs is situated next to large windows overlooking the calm waters of Sunrise Lake. A bowl of fruit is placed at the center of the table, enhancing the tranquil lakeside setting.

Cottage in Middleton

4.96 out of 5 average rating, 199 reviews

☀ 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!

Guest favorite

The exterior view of a two-story cottage showcases a modern design with light-colored siding and multiple windows. A welcoming front staircase leads to the entrance, complemented by landscaped grounds and stone details. Nearby, similar cottages form a cozy community atmosphere.

Home in Laconia

4.88 out of 5 average rating, 113 reviews

The Cottage on Paugus Bay- Lake Winnipesaukee

Enjoy peace and tranquility along the shores of Winnipesaukee's Paugus Bay. This Brand New waterfront Cottage is one of the most popular in Lakes Region and is central to all the Lakes Region has to offer. Along the western tip of the lake, easy access to I-93. The community comes with a day dock and easy access to boating and other lake activities. Come back year after year. We love repeat guests and offer discounts for second stays!

Top guest favorite

Two adirondack chairs, one red and one teal, are positioned on a sandy area overlooking a calm lake. Lush greenery surrounds the space, with small shrubs and trees framing the water view. The scene conveys a serene and inviting outdoor setting.

Cottage in Middleton

4.98 out of 5 average rating, 109 reviews

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.