
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.

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
4.89 out of 5 average rating, 240 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.
4.99 out of 5 average rating, 243 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.
4.98 out of 5 average rating, 221 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.
4.89 out of 5 average rating, 56 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.
4.79 out of 5 average rating, 145 reviews
The Nutty Bird Lakehouse
Charming lakefront featuring 2 cozy bedrooms comfortably accommodating up to 4 guests, w/2 bathrooms. Nestled in nature, this home offers breathtaking lake views—perfect for relaxing with a good book and a hot cup of coffee. Enjoy the propane firepit on lower deck. For those looking for adventure, each season brings unique activities: swim, hike, and fish in the summer, or enjoy ice skating, sledding, snowshoeing, & scenic drives in winter. Embrace the beauty and tranquility year-round!
5.0 out of 5 average rating, 39 reviews
Clean & Cozy 2BR | Great Central Location
Unwind in our 2nd floor apartment across from Lake Quinsigamond with all the essentials for a comfortable stay. Work remotely while facing the lakeview. Super close to UMass Memorial, UMass campus, and just minutes away from Starbucks, Whole Foods, TraderJoe's and many more. Surrounded by many restaurants with great variety of taste. Easy access to the highway. Escape the ordinary and make this homy lakeview apartment your home away from home. Book now for a delightful experience!
4.9 out of 5 average rating, 150 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)
4.98 out of 5 average rating, 153 reviews
Stunning Sterling Sanctuary: Unwind on the Water!
Feel your worries drift away along the freshwater when you stay at this spacious 3-bedroom, 1.5-bath Sterling vacation rental! Nestled on the serene shores of East Waushacum Pond, this home ensures a fun-filled stay for all. Spend your days exploring the water-by kayak or paddle board-and put your toes in the sand at Sterling Town Beach! When the sun sets, cook a delicious dinner on the gas grill and roast s'mores over the fire for dessert. Adventure is calling -book now!
5.0 out of 5 average rating, 38 reviews
2BR Spacious Yacht - Heat & AC- On Freedom Trail
The coolest way to stay in Boston: not a water view — you're ON the water. Carpe Diem II is a yacht in Charlestown Navy Yard with 2 queen staterooms, each with a private bathroom and shower, for up to 4 adults. Fall asleep to the harbor rocking you, have dinner and cocktails on the aft deck as boats cruise past, and stay comfortable with central A/C and heat. The Freedom Trail, North End, and Downtown are steps away. Hotels have views. You'll have the harbor.
4.96 out of 5 average rating, 159 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.
4.94 out of 5 average rating, 143 reviews
Our Pondside Cabin
Charming log cabin retreat equipped with modern amenities and conveniences! Just 3 minutes from Wachusett skiing/hiking, 8 minutes to Great Wolf Lodge and 9 minutes to Harrington Farm. Whether you're planning a peaceful retreat or an active adventure, our cabin offers the best of both worlds. Book your stay today and experience the perfect blend of rustic charm and modern comforts. We can't wait to welcome you to our happy place!
4.97 out of 5 average rating, 128 reviewsPopular amenities for Middlesex County waterfront rentals
Waterfront apartment rentals

City Sanctuary Private Terrace and Ocean Views
4.87 out of 5 average rating, 116 reviews
The Herons Nest
4.96 out of 5 average rating, 25 reviews
Cute family getaway near Boston
4.83 out of 5 average rating, 80 reviews
The Outlaw's In-Law
5.0 out of 5 average rating, 40 reviews
Barred Owl Retreat: Sunny 4 Bdr Apartment
4.94 out of 5 average rating, 84 reviews
Boston Skyline Stay | 1BR + City Views
5.0 out of 5 average rating, 61 reviews
Luxe Duplex nr Beach Seaport/Convention Cntr BCEC
4.96 out of 5 average rating, 27 reviews
East Boston Apartment | 5 Min from Logan Airport
4.89 out of 5 average rating, 37 reviewsWaterfront house rentals

Waterfront Retreat | Dock, Kayak & Lake Views
4.95 out of 5 average rating, 19 reviews
Charming lakeside cottage.
4.89 out of 5 average rating, 57 reviews
Quiet Entire House 2Br/2Ba Walk to Train/Colleges
4.72 out of 5 average rating, 18 reviews
Lake House near Boston 1
4.79 out of 5 average rating, 57 reviews
Hidden Gem near Boston w/ Private lake access
4.83 out of 5 average rating, 48 reviews
Riverfront Boston Retreat w/Parking & Backyard!
5.0 out of 5 average rating, 6 reviews
Luxury lake retreat- pool, fire pit, trails
4.76 out of 5 average rating, 38 reviews
Renovated Lakefront 5BR • Sunsets • Sleeps 10-12
4.9 out of 5 average rating, 41 reviewsWaterfront condo rentals

Eastie near the airport Great location
4.87 out of 5 average rating, 60 reviews
Dreamy Waterfront Condo | 5★ Location, ♛ King Beds
4.76 out of 5 average rating, 90 reviews
★ PRIVATE Condo in Prime Location ★
4.73 out of 5 average rating, 349 reviews
Private room next to the Main Street and lake
4.89 out of 5 average rating, 101 reviews
2bed apt cozy modern east Boston
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- Fenway Park
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- Gillette Stadium
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