Vacation rentals in Winchester

5 out of 5 average rating, 12 reviews

A classic two-family residence features a white exterior and a welcoming entrance. The property showcases a front porch with white railings and steps leading to the door. Lush greenery surrounds the home, including well-maintained shrubs and flowering plants along the walkway.

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"

4.98 out of 5 average rating, 194 reviews

A private patio area includes a round table with six chairs and a lounge chair, all set on a stone surface. A large umbrella provides shade. The view overlooks a serene lake with sailboats and lush greenery along the shore.

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.

4.93 out of 5 average rating, 335 reviews

A quaint countertop setup features a decorative teapot with colorful patterns alongside a bag of gourmet coffee. A small dish holds assorted creamers and a jar of honey, all placed on a textured surface, with a white canister in the background.

Apartment in Medford

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.

4.96 out of 5 average rating, 71 reviews

A charming cottage with solar panels is reflected in the calm pond, surrounded by vibrant green lily pads. Pink water lilies float gently on the surface, enhancing the natural beauty of the setting. Lush trees create a serene backdrop, adding to the peaceful ambiance.

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

An outdoor seating area with two light blue chairs and a small table is set on a stone patio surrounded by well-kept grass. Colorful flowers bloom nearby, and a wooden privacy fence adds a sense of seclusion.

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

A modern kitchenette is featured with stainless steel appliances, including an oven and refrigerator. A spacious gray sectional sofa is positioned on a geometric patterned area rug. Bright windows allow natural light to illuminate the room, complemented by decorative mirrors and a potted plant.

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, 102 reviews

A welcoming porch area is featured, with a round dining table under a large umbrella, surrounded by colorful planters. Two rocking chairs are positioned nearby, while soft lighting adds warmth to the inviting space.

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

A two-story house is set in a green landscape, surrounded by trees and shrubs. A clean driveway leads up to the entrance, while a white gate adds an element of charm. Sunlight illuminates the scene, highlighting the house's inviting exterior.

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.

5 out of 5 average rating, 30 reviews

A serene backyard is showcased with natural stone seating arranged around a central fire pit. Surrounded by lush greenery, a charming three-story building is visible in the background, featuring multiple windows that allow for ample daylight.

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

A wooden tray is arranged with a coffee maker, two ceramic mugs, and a container of coffee creamer. Various pods and snack bars are neatly organized within the tray, offering a cozy coffee and tea station.

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!

4.93 out of 5 average rating, 58 reviews

A back patio area is featured with a ping pong table and several seating options. A fenced swimming pool is visible, surrounded by greenery. The concrete floor provides a spacious environment for outdoor activities, and the overall setting offers a blend of privacy and openness.

Guest suite in Arlington

Spacious 1-BR apt+parking+laundry. 2nd BR option

Private 1-bedroom apartment suite near the Arlington/Winchester town line, Upper Mystic Lake, and conservation land. The bedroom is newly renovated and has a queen bed. Large living room. Small, functional kitchenette and eating area. Washer/dryer. Second bedroom available for additional fee. Parking in driveway for 1 car. it's a short walk to the 350 bus (~25-min ride to Alewife Red Line subway station.) Strong Wifi. TV with Roku (BYO streaming; no cable channels)

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Other great vacation rentals in Winchester

Private room in Arlington

A well-appointed kitchen features wooden cabinets and a tile floor. A round table with wooden chairs is positioned in the foreground, accompanied by a small potted plant. The kitchen is brightened by natural light coming through a window, showcasing a seamless connection to the dining area.

4.78 out of 5 average rating, 215 reviews

Next to Cambridge,close to T, the 1st of 4 rooms

JaredRating, 5 stars4 weeks ago

Thank you for a great stay

A living room area features a comfortable beige sofa arranged around a circular coffee table. A large rug with geometric patterns covers the floor. A television is mounted on the wall, and wooden accents and richly textured panels add warmth to the space.

Private room in Winchester

4.7 out of 5 average rating, 23 reviews

Dream room with working space

JaquelineRating, 5 stars2 months ago

Amazing...If I go back to Boston...I will definitely stay there!👏🏻😊

Private room in Arlington

A garden area is illuminated by string lights, casting a warm glow over a wooden table and chairs. Various plants are arranged on the ground, including leafy greens and climbing vines, creating a cozy outdoor dining space.

4.79 out of 5 average rating, 19 reviews

1bedroom_B_Organic Veggies Garden｜Workspace

KenRating, 5 stars1 month ago

Xiaowen's Airbnb is in a great location in a great town — quiet, yet walkable to many amenities. The few times I had to drive somewhere, I was able to coordinate with the other guests to get in and out of the single-file driveway. (On-street parking is tight during the day, when a nearby school is in session.) The bedroom was spacious and clean, and the Wi-Fi was great for working remotely. The hosts, who share the common areas, put out various items for breakfast, including copious bacon. I opted for my own food, though I didn't cook in the kitchen other than to use the microwave. Thanks for having me!

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

A wooden staircase with a handrail leads down to the lower level. The steps are illuminated by natural light, revealing a welcoming entryway with light-colored walls and a glimpse of the hallway beyond. The flooring features a modern brown finish.

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

A three-story historical house with a yellow exterior features a wraparound porch and multiple gables. Lush greenery surrounds the property, and a driveway accommodates a parked vehicle. The evening sky casts a soft glow over the charming architecture.

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

A spacious outdoor deck features a black wicker seating arrangement, including a coffee table and several chairs. Potted plants add greenery, while a white folding table with flowers offers a pop of color. The surrounding view includes residential homes and a clear sky.

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.