Vacation rentals in Winchester

5 out of 5 average rating, 16 reviews

A glass-paned door allows a view into a hallway leading to a well-lit kitchen. The hardwood floor extends into the space, and light fixtures along the ceiling provide illumination. Soft ambient light is seen towards the back, suggesting a welcoming atmosphere.

Apartment in Winchester

Winchester Apartment on Greenway

Updated apartment with hardwood floors, full kitchen and washer/dryer, next to Davidson Park, Tri-Community Greenway and the Community sport complex. A wonderful short walk down the Greenway takes you to Leonard Pond for tennis, pickleball, soccer or frisbee. A 20-minute walk down the Greenway takes you to Winchester Center for restaurants, shops and train to Boston. Or walk four blocks east to explore the 2,000-acre Middlesex Fells Reservation. Route 93 access is less than a 5-minute drive.

4.98 out of 5 average rating, 202 reviews

A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.

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.

4.63 out of 5 average rating, 35 reviews

An inviting bedroom is showcased, featuring two queen-size beds with white linens. A brick fireplace serves as a focal point, and a wooden desk and chair are positioned beside a window, allowing natural light to illuminate the space. The walls are painted in a soft yellow hue.

Home in Winchester

House on A+ school area w/AC & W/D

Fabulous opportunity to stay in a prestigious school area & a historic residential town of Winchester, MA. It’s in a beautiful, quiet, & safe neighborhood on the west side of Winchester, MA, near Lexington, Arlington, & Woburn towns. Close to historic landmarks, restaurants, elementary school, highway, & public transportation. The in-law suite with a separate entrance is part of a single-family house on the back of an A+ elementary school. Relax with your friends & family at this peaceful place

A spacious living area is presented with a comfortable sofa and an elegant armchair. A dark coffee table sits at the center, while a dining table is visible in the background. Natural light illuminates the room through the windows, enhancing the cozy atmosphere.

4.95 out of 5 average rating, 195 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

4.96 out of 5 average rating, 73 reviews

An individual is skating on a frozen pond in front of a dark blue cottage adorned with solar panels. The cottage is surrounded by trees and snow-covered ground, creating a serene winter scene.

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.

A comfortable living room is showcased with a blue sofa and two light-colored armchairs. A coffee table sits in the center, adorned with decorative items. Warm wood flooring complements the subtle hues of the walls, while soft lighting enhances the welcoming atmosphere.

5 out of 5 average rating, 158 reviews

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.

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.

4.84 out of 5 average rating, 45 reviews

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, 166 reviews

A spacious living area features a comfortable sofa adorned with textured pillows and a cozy throw. A wooden coffee table holds magazines and a remote. Natural light enters through a nearby window, enhancing the soft, neutral decor.

Guest suite in Woburn

Relaxing and Comfortable Home Away From Home

Privacy and comfort in complete lower level of this home. Private entrance and no shared space all within 5 minutes of shopping/restaurants and major highways. The space features a large kitchen w/dining area for 4pp, 1 bedroom with queen sized bed , living room with 65 inch tv with full cable. 1 full Bathroom with shower and tub. Washer and dryer are also included. Professionally maintained and enclosed backyard and patio area for outdoor seating.Full sized bed in the bonus room.

A private outdoor area features a spacious hot tub surrounded by wooden walls and deck flooring. Soft lighting is provided by string lights overhead. A small table sits nearby for convenience, and a patterned rug adds a touch of comfort to the space.

4.93 out of 5 average rating, 165 reviews

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.

4.9 out of 5 average rating, 220 reviews

The exterior of a historic gothic cottage is shown, featuring a stone facade and multiple large windows. Surrounding greenery and trees provide shade to the yard, enhancing the serene setting. A well-maintained lawn with a variety of plants is visible in the foreground.

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!

4.94 out of 5 average rating, 62 reviews

A spacious bedroom is presented with a queen bed, dressed in a soft, striped blanket. A bedside table, featuring a lamp, complements the decor. Natural light filters through a window, which is adorned with light fabric shades, creating a calm and inviting space.

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)

4.97 out of 5 average rating, 137 reviews

A private entrance to the basement suite is framed by a modern railing and steps leading down. Lush greenery surrounding the entrance enhances the serene setting, while a light fixture is positioned above the door. A children's playset can be seen in the background.

Guest suite in Lexington

Modern Farmhouse Suite in Historic Lexington

Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests

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Popular amenities for Winchester vacation rentals

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Free parking on premises

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Other great vacation rentals in Winchester

Private room in Cambridge

4.93 out of 5 average rating, 383 reviews

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Private room in Arlington

4.89 out of 5 average rating, 28 reviews

Charming Zen Flat

Private room in Winchester

A historic Victorian home is depicted, featuring a wraparound porch with white columns and multiple gabled sections. Lush greenery surrounds the property, and a spacious front lawn leads to a set of white stairs leading to the entrance.

4.89 out of 5 average rating, 18 reviews

Entire 3rd Floor Suite in Historical Victorian

Private room in Billerica

A cozy bedroom is furnished with a spacious bed covered in a blue blanket. A small desk with a chair sits beside the bed, and a bottle of water rests on the desk. Natural light filters through a nearby window, illuminating the warm tones of the walls.

4.89 out of 5 average rating, 37 reviews

Room B. Full bedroom - Cozy/Private/Fast Wi-Fi

Private room in Arlington

4.76 out of 5 average rating, 54 reviews

Jo's Jasmine White in shared apt-ask abt parking

4.98 out of 5 average rating, 44 reviews

A cozy bedroom with green walls features a bed draped in a patterned green blanket. A lamp provides illumination beside the bed, and a small desk is positioned near a window adorned with dark blinds. A radiator is visible against one wall.

Private room in Medford

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

4.9 out of 5 average rating, 41 reviews

The living room features a bright green wall and three windows adorned with wooden blinds. A dark brown coffee table is centered on a multi-colored area rug, accompanied by a black leather couch and a second seating area. A flat-screen TV is mounted on the opposite wall.

Private room in Medford

Clean Cozy, Full Bed, desk, 32"monitor, A/C,fridge