Holiday houses in Winchester

5 out of 5 average rating, 12 reviews

Home in Winchester

3 Bedroom Boston-area Gem

Your family will be 12 minutes to downtown in this exclusive Boston suburb! This is an older home (built in 1907!) It has the charms of a New England Victorian home. You can expect original hardwoods and wood detailing. The air-conditioning is supplied by window units, not central a/c. The Wedgmere stop in Winchester, on the Lowell train line goes into North Station in Boston. From North station, you take the green line to Boston University/Longwood Medical Area on the Subway, known as the "T"

5 out of 5 average rating, 44 reviews

Cottage in Arlington

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!

4.98 out of 5 average rating, 194 reviews

Apartment in Arlington

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.

4.96 out of 5 average rating, 72 reviews

Cottage in Winchester

The Little House - a historic New England cottage.

This old fashioned New England cottage in a pocket of wooded suburbs just 9 miles from Logan Airport. 4 miles from Lexington Green where the revolutionary war began. Inside the 128 beltway, its an oasis of calm in the heart of Metro Boston. Keyless entry for easy check in. A highly sought location for ice skating in winter. In summer, enjoy a chorus of frogs every night & ample wildlife sightings. Your hosts live next door, in a quiet, family neighborhood. Kids are welcome, parties are not.

5 out of 5 average rating, 148 reviews

Apartment in Woburn

Charming 1 BR private entrance apt commuters dream

Newly renovated, spacious 1 B/R apartment. Featuring a private entrance, kitchen with all new stainless-steel appliances, eating/office area, living room and separate bedroom with a Queen-sized bed, streaming cable & WIFI connections, exclusive outdoor space and off-street-parking. Minutes to Rt 95, Rt 128, Rt 93. Easy drive to all major local business, hospitals, mass transportation , airport & commuter rail less than 2 miles. Minutes to Woburn center, Winchester center, shopping & dining.

4.86 out of 5 average rating, 22 reviews

Apartment in Woburn

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

4.98 out of 5 average rating, 103 reviews

Guesthouse in Melrose

Jimmy & Donny's AirBnB

Beautiful, 2 level guesthouse! Private entrance, bedroom/bath/living area. NOTE: BEDROOM/BATHROOM ON SECOND FLOOR UP SPIRAL STAIRCASE. Large porch. Melrose is located 7.5 miles north of Boston, 2 convenient train stops, 20 minutes away, into downtown Boston. A short walk to The Fells Reservation, hiking & kayaking, or visit the Stone Zoo. We have Italian/Seafood/Mexican/Spanish/Mediterranean & Revolutionary Style Tavern restaurants in Melrose. Owners always on property. NO PETS/NO KIDS.

5 out of 5 average rating, 30 reviews

Home in Woburn

Large House- 16 mins to Boston + on site parking

Make yourself at home in this 4-bedroom Woburn retreat. With 3 queen bed, 1 full beds, and 2 twin bed, there's plenty of space for everyone to get a good night's sleep. The adorable living room features a cozy sofa bed, perfect for lounging and watching movies. The open kitchen leads to the dining room for family dinners. Enjoy the convenience of amenities like a hair dryer, washing machine, AC, WiFi, and heating. The bathrooms are equipped with showers for a refreshing start to your day.

4.93 out of 5 average rating, 239 reviews

Home in Stoneham

Entire Apartment in Stoneham

Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

5 out of 5 average rating, 31 reviews

Apartment in Medford

Garden Home by the River - Free Parking

Quiet and spacious apartment with lots of natural light. Surrounded by trees, close to nature, and steps from a walking trail around the Mystic river. Free parking in the driveway with public transit to Boston, Cambridge, and Somerville. Dedicated working space with reliable wifi. Close to the Fells (hiking, running, biking), Arlington Center (groceries, coffee, restaurants), Tufts University, Minuteman Greenway (bike to Lexington & Concord), and Mystic Lake (swimming & boating).

4.94 out of 5 average rating, 152 reviews

Apartment in Woburn

Your Cozy 1 BR Apt & Relaxing Retreat

Welcome to your romantic 1-bedroom apartment in Woburn, the ultimate escape for couples looking for relaxation and charm. Enjoy a private jacuzzi 🛁 and a cozy fire pit 🔥—ideal for creating unforgettable memories. Step right out from the bedroom to the jacuzzi and outdoor space, allowing you to unwind in the soothing waters while enjoying the warm ambiance of the fire pit. Perfect for a romantic retreat, this intimate space provides everything you need for a truly enchanting stay.

4.89 out of 5 average rating, 205 reviews

Guest suite in Medford

Beautiful 1 Bedroom, 1 Bathroom in Medford

Come stay in this recently renovated, very comfortable space situated in a quiet neighborhood across the street from the Brooks Estate woods, just outside of Boston. The house itself is a historical gothic cottage built in 1856 and is the 2nd oldest home in the area. The space is in a historic single family home and both the bedroom and bathroom are 100% PRIVATE and separated from the rest of the house with a private entrance. It's on the first floor so there are no stairs!

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4.88 out of 5 average rating, 26 reviews

Private room in Medford

Large space room

JohnRating, 5 stars8 months ago

We really enjoyed our stay - Ivone is a wonderful host and her home is in a great location. It was quiet - lots of room. We liked that it was centrally located - we wanted to be able to get into downtown Boston easily, plus be able to visit other parts of the greater Boston area. If you want to experience what one of the Boston area neighborhoods is like, it’s a great option!

4.82 out of 5 average rating, 22 reviews

Private room in Woburn

A quiet place to spend a few days

JonRating, 5 stars3 months ago

This was exactly what we needed for a quick stop over in Woburn. The bedroom and bathroom were clean and the host was very friendly.

Private room in Winchester

5 out of 5 average rating, 3 reviews

Bedroom in historical house

JenniferRating, 5 stars3 weeks ago

This is a gem in the town my kids grew up in… a perfect spot to feel at home and reconnect with friends ! Clean, spacious, and close to both boston and the charming town of Winchester !

5 out of 5 average rating, 15 reviews

Private room in Reading

Cozy Room Private Bath Direct Train to Boston

HelenaRating, 5 stars1 month ago

Our stay at Ruslan and Yaya's was just wonderful. The two, as well as their lovely dog and cat have been warm and welcoming. The place was easy to reach and offered a good spot to park to further go to Boston by train. The bedroom as well as the bathroom are lovingly furnished, were spottless clean and exceeded our expectations. Ruslan and Yaya are very communicative, help you with all your questions and are all in all really good hosts. Thank you very much for accomodating us, we really enjoyed our stay.

5 out of 5 average rating, 32 reviews

Private room in Medford

Free Parking, Private Bath, Only 10min to Boston

LauraRating, 5 stars5 days ago

We stayed one night which we booked at the last minute and Armagan was responsive and everything went smoothly. Easy to get in the building, good instructions. The room was large and very clean. The bed was comfortable. The bathroom was spotless and the water pressure was great. Good restaurants close by on Medford Square and my husband took the pup for a run along the Mystic River. We were so happy that Armagan was willing to host our dog as well. The price was a good value and we were able to get into Boston easily for our appointment the next day We would definitely stay again! Thank you!

4.97 out of 5 average rating, 39 reviews

Private room in Medford

"Tree-house" single room in cozy home, Medford

ChristineRating, 5 stars2 weeks ago

Linda is amazingling devoted to her hosts. I do appreciated to exchange with her. This is the way I see my holidays. To go to Boston needs a ten-minute walk, 2 buses lead to the train to Boston, easy-peasy. And now... Enjoy!