Holiday rentals in Punkatasset Hill

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Top-rated holiday rentals in Punkatasset Hill

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Top guest favourite

Home in Billerica

Family Retreat | Huge Yard, Playground & 5BR Home

Welcome to our spacious 5BR home, perfect for families, groups, and extended stays. Enjoy a large private yard with playground, comfortable living areas, and plenty of space to relax. Conveniently located near Wilmington Station with easy access to Burlington, Chelmsford, and Lowell (Boston about 21 miles away), this home is ideal for relocations and visiting professionals. Driveway parking, fast WiFi, and a fully equipped kitchen provide everything needed for a comfortable, stress-free stay.

4.97 out of 5 average rating, 70 reviews

Top guest favourite

Flat in Woburn

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

4.94 out of 5 average rating, 253 reviews

Guest favourite

A spacious living room area features hardwood floors and large windows allowing natural light. A dark wood cabinet holds a television, while a sofa and a colorful chair provide seating. An elegant kitchen island with seating is positioned in the background, showcasing warm wood cabinetry.

Flat in Lexington

Warm home in Lexington, walk to town, nature trail

A newly built in-law apartment, located in the historical Lexington, is welcoming travelers home. Located in a safe and friendly community, the apartment is convenient to town center, Boston, restaurants, shops, tourist spots, and Lower Vine Brook forest trail (1 min walk)! The apartment follows enhanced cleaning protocol, with thorough ventilation and disinfecting. The HVAC system is private. Checkin and checkout are easy and no-contact. Registered with the town of Lexington: STML-21-2.

4.94 out of 5 average rating, 463 reviews

Top guest favourite

A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.

Home in Chelmsford

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

5.0 out of 5 average rating, 259 reviews

Top guest favourite

A tranquil kettle pond is depicted, reflecting the surrounding wooded landscape and soft hues of the sky. The calm water creates a mirrored surface, enhancing the serene atmosphere of the natural setting.

Guest suite in Concord

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

4.98 out of 5 average rating, 153 reviews

Guest favourite

Home in Wayland

Spacious 4 bedroom home with large yard

Private and clean renovated 4 bedroom house in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 8 comfortably in 4 bedrooms. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Kids will enjoy the swingset. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27, and many colleges and MetroWest office parks.

4.9 out of 5 average rating, 132 reviews

Guest favourite

An open and spacious room is highlighted by natural light from large windows. A cozy leather settee and a small marble breakfast table with two chairs provide seating. The queen bed is dressed with a deep purple coverlet, and a decorative rug adds warmth to the wooden floor.

Flat in Concord

Cottage Suite "A" - Walk to Shops, Train, History

This is a private unit with no shared areas. It is the front corner of our house and is completely separate. However, you will share walls like in an apartment. Kitchen includes: sink, microwave, fridge, drip coffee machine, and water boiler. Private gated outside lawn and patio. History, nature, dining & shopping are very close by. Open and welcoming to ALL types of people. There is TV with internet (you can log into your streaming services) but NO LIVE TV OR CABLE

4.93 out of 5 average rating, 452 reviews

Guest favourite

The charming exterior of the 1897 home features a wraparound porch adorned with flags and seasonal decorations. A well-maintained yard displays decorative stone borders, mulch, and blooming flowers, framed by lush green trees and shrubs.

Home in Sudbury

Spacious Victorian Home | Family + Pet Friendly

Spacious historic 3 bedroom Victorian home with 4 bathrooms, set up for families and groups to stay together without feeling crowded. Period details like original staircases, pocket doors, and high ceilings add charm, while modern amenities like central air, updated baths, and a well-appointed kitchen make it easy to live in. Walk to shops and restaurants in Sudbury’s village center, with easy access to Concord, Lexington, area colleges, and Boston. Pets welcome.

4.94 out of 5 average rating, 95 reviews

Top guest favourite

A cozy living area features a spacious sectional sofa adorned with patterned pillows. Natural light filters through large windows, illuminating the wooden floor. A coffee table sits at the center, complemented by a decorative area rug. A large wall-mounted TV and a wooden dresser are visible.

Flat in Bedford

Entire private guest suite

Newly constructed, newly furnished private guest suite at the end of a dead-ended street in a quiet neighborhood. Family friendly for recreation or well suited for work. Easy access to Rt. 128 Technology corridor. Short walk to town center with shopping, library, playgrounds and restaurants. Few minutes drive to historic Lexington and Concord. Near popular Minuteman bike path leading to Cambridge. Easy access to Boston. 20+ colleges within 20 mile radius.

4.97 out of 5 average rating, 99 reviews

Top guest favourite

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

4.97 out of 5 average rating, 183 reviews

Top guest favourite

A stylish living room features a green sectional sofa complemented by colorful throw pillows. A round coffee table rests on a patterned area rug. Art pieces adorn the walls, and natural light enters through windows, illuminating the warm wooden flooring and brick fireplace.

Home in Arlington

The Brickhouz at Arlington !

Just a little bit of everything for everyone to have a spectacular time in Boston, perfect for family gathering ! A funky and quirky cozy 4-bedroom brickhouse smack right in the middle of Arlington Center. 10 mins to Harvard Square, 15 minutes to Boston and Logan airport. Sleeps 8 - 2 bathrooms. Short 1 minute walk to cafes and restaurants. Discounts available for longer stays. Strictly no parties or unapproved pets.

4.99 out of 5 average rating, 117 reviews

Guest favourite

The exterior of a modern two-story home is depicted, featuring light-colored siding and a welcoming front yard. A driveway leads to a two-car garage on the side, with a neatly maintained lawn and mature trees providing shade. A white picket fence borders the property.

Guest suite in Lexington

Modern Studio w/ Fire Pit, Play Area & Large Yard

Welcome to our cozy, modern suite in historic Lexington! Enjoy a peaceful stay with full private access, fast WiFi, Smart TV, home theater, kitchenette, and private gym with a Peloton bike. Relax by the fire pit or let the kids play outside. Just minutes from trails, Battle Green, and 20 minutes to Boston — a perfect home for families, groups, or business travelers. Certificate number: STML-24-5

4.9 out of 5 average rating, 73 reviews