Waterfront vacation rentals in Middlesex County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Middlesex County

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

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Guest favorite

A spacious living area features a large sectional sofa complemented by plush cushions. A coffee table with a classic game set is positioned in front. The room is illuminated by soft overhead lighting, with a grand staircase visible in the background leading to a second floor.

Home in Berlin

4.91 out of 5 average rating, 33 reviews

Luxurious Spacious Haven Retreat - Close2Boston

Welcome to our Luxurious Spacious Haven Retreat! This High-end home offers unparalleled comfort and elegance. Nestled in a serene neighborhood, and top-notch amenities. The gourmet kitchen, cozy bedrooms, and modern bathrooms provide a perfect blend of luxury and convenience. Ideal for families or groups seeking a tranquil escape with all the comforts of home. Close to many restaurants and shopping The Shops of Highland Commons and the charming downtown Hudson its minutes away. Gorgeous views.

Top guest favorite

A quaint cabin is positioned among trees, softly lit at night. An illuminated entrance is framed by colorful pots and surrounded by a cozy seating area with an Adirondack chair. Flickering firelight adds warmth to the inviting outdoor space.

Cabin in Littleton

4.99 out of 5 average rating, 200 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Guest favorite

The exterior of the cottage features a multi-tiered deck with white railings and a set of stairs leading to lush green grass. String lights hang above, and comfortable chairs are arranged for relaxation. Large windows provide a glimpse of the interior spaces, accented by natural surroundings.

Home in Westminster

4.9 out of 5 average rating, 201 reviews

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Top guest favorite

A cozy living area features a dark sectional sofa and a light wood coffee table positioned on a textured area rug. A television is mounted on the wall across from the seating, complemented by a small lamp on a side table. Natural light filters through multiple small windows.

Apartment in Wayland

4.96 out of 5 average rating, 26 reviews

Cozy lakeside retreat

Take it easy at this unique and tranquil getaway a perfect spot to recharge and enjoy all Dudley Pond has to offer.Relax on the deck overlooking the water OR explore on a canoe, kayak, or paddleboard OR walk to TheChat (an old speakeasy) for yummy drinks and food. Centrally located in the Metrowest suburbs close to the Mass turnpike and public transportation to downtown Boston. Close to Babson, Wellesley College, Boston University, Brandeis, Framingham State for graduation or parent weekends.

Guest favorite

A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.

Apartment in Arlington

4.98 out of 5 average rating, 203 reviews

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

Top guest favorite

An individual is skating on a frozen pond in front of a dark blue cottage adorned with solar panels. The cottage is surrounded by trees and snow-covered ground, creating a serene winter scene.

Cottage in Winchester

4.96 out of 5 average rating, 73 reviews

The Little House - a historic New England cottage.

This old fashioned New England cottage in a pocket of wooded suburbs just 9 miles from Logan Airport. 4 miles from Lexington Green where the revolutionary war began. Inside the 128 beltway, its an oasis of calm in the heart of Metro Boston. Keyless entry for easy check in. A highly sought location for ice skating in winter. In summer, enjoy a chorus of frogs every night & ample wildlife sightings. Your hosts live next door, in a quiet, family neighborhood. Kids are welcome, parties are not.

Superhost

The spacious living area features a comfortable sofa paired with a coffee table. A dining space with wooden chairs and a well-equipped kitchen is visible in the background, complemented by modern appliances and natural light from large windows.

Apartment in Waltham

4.85 out of 5 average rating, 110 reviews

2bed/2bath Apt at Waltham Landing. Corner Unit

This apartment complex was built in 2016. It is 1 block from The Charles River and Waltham's famous Moody Street, aka "Restaurant Row." Across the street from Waltham Station: Fitchburg Line - Commuter Rail. Bentley and Brandeis are 1 mile away. Monthly rentals accepted (inquire for best rate), discounts for groups and long-term rentals. Perfect for business travelers, families, anyone in between housing or visiting town! Free parking in the parking lot. Yes there is an Elevator.

Guest favorite

A spacious yacht is docked along a wooden pier. The boat features a white exterior with a flybridge and is surrounded by calm waters. In the background, other boats and waterfront buildings can be seen under a clear blue sky with a few fluffy clouds.

Boat in Boston

4.95 out of 5 average rating, 138 reviews

2BR Spacious Yacht - Heat & AC - On Freedom Trail

Escape the hustle and bustle of the city and unwind aboard Carpe Diem II, a yacht with 2 comfy queen staterooms for up to 4 adults. Each stateroom has a private bathroom and shower. Unwind on the aft deck with meals and cocktails as the boats sail by on the harbor, or warm up or cool off inside with central A/C and heat. Located in Charlestown Navy Yard, steps to Freedom Trail, North End, and Downtown. Book now and enjoy the unique charm of living on the water in this historic neighborhood.

Top guest favorite

A tranquil kettle pond is depicted, reflecting the surrounding wooded landscape and soft hues of the sky. The calm water creates a mirrored surface, enhancing the serene atmosphere of the natural setting.

Guest suite in Concord

4.98 out of 5 average rating, 130 reviews

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Guest favorite

A serene landscape is portrayed, featuring tall trees framing a clear view of Bare Hill Pond. Bright foliage and fallen leaves cover the grassy area, while the still water reflects the surrounding natural beauty. Soft light filters through the trees, enhancing the peaceful atmosphere.

Guest suite in Harvard

5 out of 5 average rating, 7 reviews

Picturesque Waterfront Getaway

Relax and enjoy four seasons of beauty on Bare Hill Pond in Harvard, MA! Nearby are conservation trails, Prospect Hill, and a cozy general store. Located on the lower level of our family home is a private unit with kitchen, dining area, living room, bedroom with queen bed, and full bathroom. There's radiant heat, polished concrete floors and a gas fireplace. The patio is perfect for morning coffee, chilling, grilling and cocktails at sunset. Linens provided.

Guest favorite

A charming brick building is framed by lush green foliage. Large windows are adorned with flower boxes, displaying red flowers. A blue front door adds a pop of color while welcoming visitors to the entrance, which is highlighted by warm lighting.

Apartment in Boston

4.88 out of 5 average rating, 105 reviews

City sanctuary - garden terrace - ocean view

Large sunny, private studio with stunning views and terrace overlooking the ocean, garden and JKF library, across the street from famous historic park Dorchester Heights. 2 blocks from beach. Close to convention center, airport, downtown, bus and trains. Easy walk to great local shops and haunts! Unit now equipped with Forbes #1 vetted best mattress - the Nectar Premier Hybrid Copper Queen mattress and there is a full size pull out futon

Guest favorite

A welcoming family home is set in a lush green landscape, featuring beige siding and a dark shingled roof. The property includes a driveway leading towards a two-car garage, surrounded by thoughtfully maintained gardens.

Home in Westminster

4.94 out of 5 average rating, 130 reviews

Wachusett Mountain Get-Away

This family home is spacious and accommodating for those looking to relax while away from the ski slopes or simply wanting to get away from the city. Situated nearby a plethora of hiking and mountain biking trails, lakes for fishing and paddling, the home is perfect for those craving the great outdoors. The home is 6 min from Wachusett Mountain Ski Resort, 3 min from the Wachusett Brewery, and 1 min from the 1761 Old Mill Restaurant.