Vacation rentals with a kayak in Middlesex County

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. Heating/AC provided by mini splits & 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.

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.

Garden Apartment for Vacation & Business Travelers

The perfect place to rest, relax or work. Visit universities, Salem or family and friends in the area. This English Basement apartment is located on the Mystic River, 10 minutes from Harvard University in Cambridge and 20 minutes from the City of Boston. Enjoy many local outdoor amenities including the Mystic Lakes, parks, playgrounds, tennis/pickleball/basketball courts and jogging paths, all behind our house. We warmly welcome people from all backgrounds as we value and respect diversity.

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Worcester Home on Indian Lake w/ Shared Boat Dock!

Torn between a lakefront getaway and a big-city adventure? Bordering Indian Lake, this 3-bed, 2-bath Worcester vacation rental provides the best of both worlds! Not only will you have direct access to the water from the shared boat dock, but you'll also be close to college campuses, sports venues, and Union Station. Tour Clark University or grab a seat at the DCU Center or Polar Park for whatever event is in town, and later, enjoy some time unwinding with lake views from the private deck!

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!

Cozy, 2BR lake-side retreat and outdoor oasis

Our cozy, family friendly and completely remodeled lake house enjoys modern conveniences with private lake access and quick access to Boston (only 45 mins!). The vacation getaway is located on Lost Lake in beautiful Groton, MA bordering serene conservation land on 2 sides and facing a small private beach with dock. The location offers a balance of natural beauty with a convenience to amenities allowing you to get away from the fast paced city life but return at your leisure!

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!

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake, the upstairs suite has a panoramic view from the bedroom, a private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room - it feels like an apartment. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants, a casino, or tax-free shopping. We are one hour from Boston.

Secluded Rustic Lakeside Cabin - Perfect Escape

Take it easy at this peaceful and secluded lakefront getaway. Escape to our log cabin nestled in the woods on the shores of a pristine lake in Groton, Massachusetts, less than an hour from Boston. The cabin blends rustic charm with modern comfort and offers a quiet setting to relax and unwind. Enjoy lake views, fresh air, and the sounds of nature. This home is best suited for quiet family vacations and responsible adult travelers seeking a peaceful lake retreat.

Private lake "Island" near Boston

This place is a hidden gem! It is a private lake peninsula with stunning views. Very quiet. Enjoy the amazing lifestyle on Lake Quinsigamond, while being only 10min from the center of Worcester. Lots of fun things all year around and only 40min to Boston, 1.5hr to Cape Cod beaches. This 2 bedroom A-frame house and 1 BDR cabin are on a 5 acres property (2,000 feet of shoreline). Very close to UMass hospital, grocery stores, gym, restaurants, route 20 and I-90.

Newly renovated, close to Foxboro and Boston

Only 10 miles to Foxboro stadium!Private guest suite surrounded by nature and a large yard featuring a large POOL (closed Sep-May) with beach entry and pool slide. Next to Blue Hills and pond, a nature escape close to Boston! Nature trail right by your door! An additional unit with queen bed is available as well. Queen size bed, bathroom, WIFI, smart TV, kitchenette with microwave, coffee maker, toaster, fridge. Stove in a shared kitchen. Massage chair.