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.

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.

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.

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.

City Sanctuary Private Terrace and Ocean Views

WORLD CUP -TALL SHIPS -4th of July - sunny private studio in one of Boston’s most scenic neighborhoods. Private terrace, across from historic Dorchester Heights Park. LOCATION—walking distance to Castle Island, entry to Boston Harbor where ships will be at full mast. 2 blocks from beach - easy access to Seaport, downtown, airport, and public transit to Stadium for World Cup. The neighborhood is a true gem with great shops, cafés, and dining.  This peaceful studio offers a perfect home base.

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!

Quincy Escape – Coastal Getaway, Steps from Boston

Wake up to sea breezes and the charm of a coastal neighborhood just minutes from Boston. Quincy Escape is a thoughtfully renovated 4-bedroom, 2-bath home where sunlight fills every corner and modern design meets cozy comfort. The beach is only a short walk away, and with plenty of space to gather, it’s perfect for family vacations, work trips, or city adventures. Relax by the shore, enjoy nearby dining, explore Boston with ease, and let Quincy Escape be your place to unwind.

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.

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.