Waterfront vacation rentals in Milton

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Top-rated waterfront rentals in Milton

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Superhost

A serene view of a cottage perched among trees, featuring a spacious deck with blue chairs. A dock is seen below, with seating and steps leading to the water, creating an inviting space for relaxation and outdoor activities.

Cottage in Windham

4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

Guest favorite

A serene outdoor space is bordered by trees and features a gravel area with seating around a fire pit. A wooden deck extends from the cabin, providing views of the nearby river, enhancing the natural landscape.

Home in Naples

4.99 out of 5 average rating, 115 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Top guest favorite

A serene waterfront view captures a cluster of charming homes along the peninsula. Lush greenery and bare trees establish a natural landscape, while the calm water reflects the muted colors of the surroundings. The distant shoreline reveals additional residences, evoking a peaceful coastal ambiance.

Cottage in Eliot

4.99 out of 5 average rating, 140 reviews

Salty Mermaid Cottage/Boat House

This 2br home is nestled at the end of a peninsula’s over the water, 5min drive to downtown Portsmouth. Spend the day on the on deck, grilling or enjoy your own authentic Maine lobster bake, swimming and treasure hunting the shore. Also explore Kittery or downtown Portsmouth, both just five minutes away. Enjoy this freshly renovated home, water views from every room and window, all bedrooms are equipped with a/c, free WiFi and smart TVs. Fully equipped kitchen has an amazing view of the water.

Top guest favorite

A spacious living area features large windows that provide scenic views of the surrounding landscape. Comfortable seating arrangements include a light-colored sofa and armchairs, complemented by a wooden coffee table. A dining area is visible, with fresh blooms enhancing the inviting ambiance.

Apartment in Arundel

4.98 out of 5 average rating, 330 reviews

Cape Arundel Cottage 1 mile to downtown KPT

Tastefully appointed 1 bedroom apartment one mile from desirable Dock Square, Kennebunkport. This apartment features Panoramic views of the famous Cape Arundel Golf Course and Goff's Brook Tidal River. Private, secluded back deck with dining and lounge areas, Cozy furnishings throughout, King sized bed with memory foam topper, Fully Equipped Kitchen, and more! At Cape Arundel Cottage, guest experience is our highest priority! *See “other things to note” for additional important information.*

Top guest favorite

Home in Windham

4.94 out of 5 average rating, 126 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.

Superhost

A serene waterfront view showcases a sandy beach area bordered by green grass. Red Adirondack chairs are arranged around a central fire pit. In the background, calm water reflects a clear sky and nearby trees, while boats are docked along the shoreline.

Home in Barnstead

4.84 out of 5 average rating, 101 reviews

Locke Lake Waterfront Escape

Completely renovated home with private beach and waterfront. The water drops off gently making it great for young children. Variety of rafts, beach toys, kayaks, paddle boards, pedal and row boat available for use. Great fishing in the summer, and ice fishing in the winter. Outdoor deck is wonderful for entertaining. Seasonal game room in garage with shuffleboard and more. Located about 15 mins south of Lake Winnipesaukee and 30 mins from Gunstock Mountain. *Linens and Towels now included!*

Guest favorite

An aerial view of a waterfront lake house situated along the shores of Daniels Lake. The property features a spacious deck with kayaks, surrounded by trees. A sandy beach area is visible, leading to calm water, while nearby cabins are nestled among the greenery.

Home in Weare

4.97 out of 5 average rating, 73 reviews

Impressive large, 4 Bedroom Waterfront Home, King Suite

Welcome to our waterfront lake house on the shores of Daniels Lake! This 4,200 square foot, 4 Bedroom home is situated directly on the water with beach access right out your front door. Featuring 3 gorgeous bathrooms, a huge master suite with king bed and balcony overlooking the living room. This home also has a separate kitchenette in the studio suite above the garage with private deck, great for multi family vacations! The home has a total of 9 beds for flexible sleeping arrangements.

Guest favorite

A deck overlooking the water features a barbecue grill and several outdoor chairs arranged around a small table. Lush green trees provide shade, while the view of the shimmering water is visible in the background under a clear blue sky.

Home in Kittery

4.94 out of 5 average rating, 138 reviews

Gorgeous Waterfront Home with Dock and Beach

Looking for a wonderful location to enjoy a week this summer in Maine? We have a beautiful location right on the water for you and your family to enjoy. HAVE A BOAT and want to bring it with you? We have a deep water dock. Ask us about details and cost. House is on a dead end road. Come & enjoy the Maine coast! We are located 2 miles from Portsmouth, and there are numerous activities to do in this area. Golfing, Boating, Swimming, Outlet shopping and of course the Beach!

Top guest favorite

Home in Scarborough

4.97 out of 5 average rating, 32 reviews

Breathtaking waterfront home near Pine Point Beach

Breathtaking sunset views, ever-changing scenery of sky and water, this is a dream location for kayakers, bird watchers, swimmers, and fisherman. Enjoy the changing of the tides and abundant sounds of nature from one of two decks, your back lawn or sunny master deck. Beautifully renovated and designed this property features a private master bedroom suite with private deck, two bedrooms and full bath on the 2nd floor, 3rd floor is open space for additional sleeping space.

Guest favorite

A spacious living area features high ceilings with exposed wooden beams and large floor-to-ceiling windows that provide abundant natural light and views of the surrounding trees. A stone fireplace serves as a focal point, complemented by comfortable seating and a richly textured area rug.

Chalet in Naples

4.96 out of 5 average rating, 106 reviews

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Top guest favorite

A garden featuring blooming purple flowers sits in the foreground, overlooking a calm lake reflecting the clear sky. Boats are docked nearby, and distant greenery hills rise along the shoreline, providing a serene backdrop to the water.

Condo in Wolfeboro

4.96 out of 5 average rating, 134 reviews

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.

Top guest favorite

A modern kitchen features an island with bar stools and white shaker cabinets. Bright lighting is provided by pendant fixtures above. Large windows showcase waterfront views, while a dining area is visible, with a colorful striped rug under the table.

Apartment in Downtown Portland

4.96 out of 5 average rating, 113 reviews

"Henry" Penthouse Waterfront Suite

2023 City of Portland Registration #20185280-ST Penthouse suite with modern amenities, exposed beams and brick, whitewashed poplar walls. Rooftop deck with views of harbor and city. Separate master suites with custom showers and one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops. Please note: animals (including assistance animals) not allowed due to owner's health.