Beachfront holiday rentals in Middlesex County

Quiet Entire House 2Br/2Ba Walk to Train/Colleges

Entire 2 story colonial style 2Br single family in Wellesley Sq. The most convenient location in town! Easy access to Wellesley and Babson Colleges, walk to train to Boston, summer camps, Whole Foods grocery, restaurants. Large, lush fenced backyard with 2 Patios. Park/sports field/tennis courts/playground just beyond our backyard. Fast WiFi, free parking, AC/heating. 3 beds + mattress, office desks, 2 bathrooms, open concept living room & piano (upon request), TV, dining room, stocked kitchen.

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

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.

Southie 3 Bed Single Family w/ Back Patio

Your whole group will enjoy lounging around the house and easy access to everything from this centrally located single family house in South Boston (Southie). The neighborhood is quiet, being equally located a few blocks from both Broadway and the beach. The comfortable open layout has plenty of natural sunlight, private patio and big comfy beds. If you're not familiar with Southie, hit the request button and come find out! The walkable neighborhood offers many excellent restaurants and bars.

Private waterfront home!

“La Casita” is a private waterfront home near Umass medical! Modern 1-2 bedroom home with a Master Bedroom on the 2nd 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.

Hidden Gem near Boston w/ Private lake access

Waterfront 3BR home 1 mile from commuter rail to Boston. 1 mile from Blue hills ski. 2.2 miles from New England's 1st and only TopGolf. This 3BR, 2.5 BA features an open floor plan w/ view of your private lake from the kitchen and dining rooms. Head downstairs to play pool, ping pong or darts. Or relax by the fire and watch tv (all streaming channels). Warmer months turns into a resort: Fishing, boating, swimming, grill, fire pit, furnished cabanas, hiking the blue hills and much much more.

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!

Just Chill'inn Cottage

Now booking for 2026 from April 19th. Just Chill’inn is a beautiful 2-bedroom, 1 bath cottage including a 4-person golfcart in a family focused seasonal resort community. Enjoy a heated family pool, toddler pool, playground. A sandy beach on a lake. For you and your 18+ guests: additional adult heated pool, hot tub, and fitness center. Pickleball, tennis, basketball courts; recreation room with ping pong table; canoes, sunfish sailboats. Restaurant & bar with pool table at the beach.

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!

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.

City Sanctuary Private Terrace & Ocean Views

WORLD CUP READY ocean views - sunny private studio in one of Boston’s most scenic neighborhoods. Step outside onto your private terrace for fresh ocean air, just across from historic Dorchester Heights Park. Location is everything—2 blocks to the beach with easy access to downtown, airport, and public transit. The neighborhood is a true gem with great shops, cafés, and dining.  This peaceful studio offers a perfect home base.

Lake House with Ski Mountain View

This charming lakefront getaway sits directly on Wyman Lake and offers spectacular views of Wachusett Ski Mountain. In the summer, enjoy boating, swimming, and relaxing by the water. In the winter, take advantage of day and night skiing just minutes away. Nestled in a peaceful, private location, the home offers the tranquility of a true retreat while still being just minutes from the highway and local amenities.