
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.

Private waterfront home!
“La Casita” is a private waterfront home near Umass medical! Modern 1-2 bedroom home with a Master Bedroom on the second floor and a multi use room that can be used as a 2nd bedroom with a full size futon. There is a 3 season porch with a dining nook which leads out to a big outdoor deck. There are multiple ceiling fans and water toys for renters use. No pets or smokers. This is a quiet, family oriented neighborhood with another home on the lot with small children so calm renters only please.

Charming Waterfront Cottage Near Cambridge/Boston
Delightful 1-bedroom guest cottage in Arlington with picturesque waterfront views and cozy interiors. Tucked away on Spy Pond, the cottage offers a peaceful retreat and a short drive to Cambridge (10 min to Harvard Square), Boston (20-25 minutes to Logan Airport), and Harvard, MIT, Tufts, BU. Comfortable furnishings and an abundance of windows overlooking the water create a bright and calming backdrop for your stay. Enjoy getting away from it all, while being close to everything you might need!

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

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.

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.

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.

2bed/2bath Apt at Waltham Landing. Middle 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.

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)

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.

Clean & Cozy 2BR Across from Quinsigamond Lake
Unwind in our comfy 2-bedroom apartment 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!

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

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.
Popular amenities for Middlesex County waterfront rentals
Waterfront apartment rentals

Modern 2Br2Ba apartment

Panoramic City-Skyline MIT/Harvard CIC Kendall Sqr

Sunny 2-Bdrm Apartment at the Barred Owl Retreat

The Outlaw's In-Law

Swan Manor Overlooking the Charles River

Luxe 2 level Apt nr Seaport/Convention Centre BCEC

Monthly Skyline Apartment

Large 2 BR | 1BA in the North End
Waterfront house rentals

Lakefront Retreat • Near Colleges • Sleeps 12

The Nutty Bird Lakehouse

Lakefront House with breathtaking sunsets!

Our Pondside Cabin

Entire House: Home Away Home

Large & beautiful home, shared pool and yard

Lake House near Boston 1

Luxurious Spacious Haven Retreat - Close2Boston
Waterfront condo rentals

Stunning Waterfront Condo with Boston Skyline View

Eastie near the airport Great location

Private room next to the Main Street and lake

Dreamy Waterfront Condo | 5★ Location, ♛ King Beds
Destinations to explore
- Guesthouse rentals Middlesex County
- Rentals with a washer and dryer Middlesex County
- Family-friendly rentals Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with outdoor seating Middlesex County
- Pet-friendly rentals Middlesex County
- Townhouse rentals Middlesex County
- Smoking-friendly rentals Middlesex County
- Rentals with breakfast Middlesex County
- Rentals with an accessible height bed Middlesex County
- Rentals with a fire pit Middlesex County
- Rentals with pools Middlesex County
- Cottage rentals Middlesex County
- Rentals with a hot tub Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with a home theater Middlesex County
- Condo rentals Middlesex County
- House rentals Middlesex County
- Rentals with beach access Middlesex County
- Rentals with lake access Middlesex County
- Rentals with a patio Middlesex County
- Hotel rentals Middlesex County
- Rentals with a kayak Middlesex County
- Loft rentals Middlesex County
- Apartment rentals Middlesex County
- Private suite rentals Middlesex County
- Rentals with an EV charger Middlesex County
- Bed and breakfasts Middlesex County
- Waterfront rentals Massachusetts
- Waterfront rentals United States
- Hampton Beach
- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- Duxbury Beach
- New England Aquarium
- Monadnock State Park
- Good Harbor Beach
- Canobie Lake Park
- MIT Museum
- Freedom Trail
- Crane Beach
- Faneuil Hall Marketplace
- Museum of Fine Arts, Boston
- Jenness State Beach
- North Hampton Beach
- Rye North Beach
- Quincy Market
- Prudential Center
- Roger Williams Park Zoo
- Things to do Middlesex County
- Food and drink Middlesex County
- Sightseeing Middlesex County
- Art and culture Middlesex County
- Things to do Massachusetts
- Sightseeing Massachusetts
- Tours Massachusetts
- Art and culture Massachusetts
- Food and drink Massachusetts
- Sports activities Massachusetts
- Nature and outdoors Massachusetts
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Wellness United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes