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Holiday rentals in Tewksbury

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Top-rated holiday rentals in Tewksbury

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A private entrance is shown, leading to a spacious deck with wooden railings. Natural light illuminates the area, while greenery and large trees are visible in the background, providing a serene and inviting outdoor space.
Flat in Woburn
4.95 out of 5 average rating, 232 reviews

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!

Guest favourite
A serene outdoor space features a winding stone path leading through lush green grass. Two comfortable chairs are positioned under a large tree, providing a shaded area for relaxation. Surrounding pine trees create a natural backdrop, adding to the tranquility of the setting.
Flat in Woburn
4.87 out of 5 average rating, 135 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!

Guest favourite
The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.
Farm stay in North Andover
4.95 out of 5 average rating, 294 reviews

Winery Studio w/ Private Hot Tub & Wine Tasting

Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

Top guest favourite
A serene lakeside view captures a vibrant sunset with the sun partially descending behind distant hills. A lone fisherman in a boat is visible on the water, while a wooden deck features seating arrangements surrounded by lush plants.
Guest suite in Tyngsborough
4.98 out of 5 average rating, 268 reviews

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, but no kitchen. 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.

Top guest favourite
Home in Chelmsford
5 out of 5 average rating, 249 reviews

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.

Superhost
Flat in Lowell
4.7 out of 5 average rating, 30 reviews

The Cozy Den

Welcome to your home away from home! This cozy and stylish apartment is thoughtfully designed with families in mind, offering a peaceful retreat where you can truly relax. Soft, comfortable furnishings and a calm color palette create a welcoming atmosphere, perfect for unwinding after a day of exploring. Within a walking distance to the MBTA (the T) and close to UMASS Lowell and Tsongas Center. Not to mention close to restaurants, museums, grocery stores and gas stations.

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
4.97 out of 5 average rating, 176 reviews

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

Top guest favourite
Flat in North Andover
4.97 out of 5 average rating, 152 reviews

3 room suite, 24 miles to Boston, British decor

Lovely new 3 Room suite with Full kitchen. Ideal suburban location. 24 miles north of Boston, close to NH border. 25 min ride to NH beaches, Hampton and Rye. About 35 mins. to Salem, MA. Close to Merrimack College and Phillips Academy. You will feel at home in this spacious apt. Enjoy British influence decor. Perfect for couples or families. Unique Outdoor Pizza Oven experience can be arranged, weather permitting. Please inquire.

Top guest favourite
A serene pool area is surrounded by lush greenery and colorful landscaping. A circular hot tub is integrated into the pool's design. Sunlight reflects off the water, enhancing the tranquil atmosphere. Outdoor seating is visible nearby, providing ample space for relaxation.
Home in North Andover
4.94 out of 5 average rating, 178 reviews

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

Guest favourite
A spacious living area features high ceilings and an open layout. A comfortable seating area includes dark recliners facing the sleeping space, which is defined by a large bed and artwork. Light enters through multiple windows, creating a bright atmosphere.
Flat in Woburn
4.97 out of 5 average rating, 113 reviews

Newly Built En Suite

Discover a stylish en-suite apartment in Woburn, MA, managed by experienced hosts. This property features a private entrance, a spacious layout with high ceilings, and a private patio. Enjoy easy access to local attractions and the convenience of a well-equipped space. Perfect for a relaxing getaway with your furry friend, this apartment offers a blend of comfort and accessibility.

Guest favourite
Barn in Carlisle
4.88 out of 5 average rating, 460 reviews

Private Studio w/ Loft Center Historic Carlisle

Charming private studio in the heart of Carlisle, perfect for 2 adults (up to 4 guests). Completely separate with no shared spaces. Close to Routes 128, 495, 35min to Boston, 10 min to historic Concord. Outdoor lovers enjoy nearby hiking, biking, and Great Brook Farm State Park. Easy access to Lowell, Nashoba Valley Ski Area, shops, and restaurants.

Top guest favourite
An outdoor patio area is showcased with a small table and two chairs set beneath an umbrella. A grill is positioned nearby, and a potted plant with vibrant flowers adds a pop of color. A privacy fence provides an enclosed feeling.
Guest suite in Woburn
4.97 out of 5 average rating, 184 reviews

Private apartment with off street parking

Enjoy your private retreat in this spacious 1-bedroom lower-level apartment, comfortably accommodating up to 4 guests. Features a fully equipped kitchen, a cozy living room with a 65" Smart TV, and access to a beautiful, enclosed backyard. Located minutes from shops and restaurants, it's the perfect blend of comfort and convenience for your stay.

Popular amenities for Tewksbury holiday rentals