House holiday rentals in Middlesex County

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Top-rated house rentals in Middlesex County

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Top guest favourite
An outdoor deck features two ornate chairs and a small table, overlooking a serene sunset. The horizon displays soft hues of orange and blue, with the silhouette of rooftops adding depth to the scene. Lush greenery can be observed nearby.
Home in Somerville
4.98 out of 5 average rating, 151 reviews

The Nest | A peaceful retreat in the city

Unwind and relax on a quiet street in the heart of Somerville. With easy access to Harvard, MIT, Tufts, and Boston, this newly updated Victorian home is a perfect base to explore all that New England has to offer. You can also visit an abundance of local restaurants and coffeeshops within walking distance. During your stay, you will enjoy full use of a smart TV, comfortable work-from-home setup, brand new washer/dryer/dishwasher/range, off-street parking, and multizone heating/ cooling systems.

Top guest favourite
The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.
Home in Holliston
4.97 out of 5 average rating, 111 reviews

All New Private Country Setting (2 Level-No Share)

We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

Top guest favourite
A comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.
Home in Framingham
4.97 out of 5 average rating, 102 reviews

Cozy en suite w/ high ceilings

 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

Top guest favourite
The kitchen features a modern layout with white cabinets and granite countertops. Stainless steel appliances, including a French door refrigerator, are complemented by a tiled backsplash. Natural light enters through multiple windows, illuminating the spacious area. Two area rugs add warmth to the tiled floor.
Home in Framingham
4.98 out of 5 average rating, 253 reviews

*Ready for Check-In*—1200ft² 2BR—25 Min to Boston

CHECK IN 12/31 — ANYTIME AFTER 7:30AM ⚡️Last Minute Discount⚡️ ⭐️Children 12+ Welcome⭐️ Welcome to our 1900s house! 1200ft² Private Apartment @ our 3-Rental Property Granite Kitchen w/Dishwasher + Essentials & Cookware Tiled Bathroom w/Bath & Shower 2 Queen Bedrooms 2 Desks & Chairs Recliner Sofa & Glider Loveseat Dining for 6 Private Entrance Driveway Parking—2 Spots Laundry in Basement 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby Deep Cleaned & Sanitized

Top guest favourite
A cozy living area is presented, featuring a modern black sofa and two soft pink ottomans. Natural light streams in through the window, illuminating the space. Decorative shelves with plants and artwork add a touch of greenery and charm to the room.
Home in Stoneham
4.93 out of 5 average rating, 308 reviews

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.

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
5 out of 5 average rating, 232 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.

Top guest favourite
A spacious bedroom is illuminated by natural light from large windows, featuring a comfortable bed with soft linens. Two plush armchairs are positioned across from a cozy sofa. A modern glass coffee table holds a magazine, while decorative elements add charm to the setting.
Home in Cambridge
4.94 out of 5 average rating, 306 reviews

Stunning urban hideaway nearby Harvard Square

Charming apartment in a 19th century Victorian house conserves its period architectural details in recently renovated comfort. Light streams into this en-suite guest residence through gracious windows. Beautiful cabinetry and bookcases offer some evening reading. Enjoy the marble bathroom and hardware floors and well-appointed kitchenette. A stone's throw from Porter Square, where bars, cafes, boutiques, and transportation options abound. Minutes to Harvard, MIT and Boston.

Top guest favourite
The kitchen area features a modern design with a sleek, round dining table surrounded by four transparent chairs. Stainless steel appliances, including a refrigerator and stove, are present, complemented by wooden cabinetry. Natural light enters through a window, illuminating the polished hardwood floor.
Home in Boston
4.87 out of 5 average rating, 225 reviews

Comfortable house w garden and parking, close to T

The house is conveniently located 15-20 mins from downtown and 25 mins from the airport by taxi. There is a train and bus stations close by and there are lots of restaurants and stores (whole foods has everything) in a walking distance. There is a driveway parking that fits 3 cars. The house offers 7 sleeping places which is perfect for families and groups however there is no living room. Great place to stay with dogs as there is a backyard and lots of walking options.

Guest favourite
A dining area is shown with a long wooden table set with neutral placemats. Four tan chairs surround the table, and a decorative flower arrangement is placed at its center. Natural light filters through three large windows, framed by soft gray shades.
Home in Newton
4.91 out of 5 average rating, 175 reviews

Convenient 2BR Condo W/Private Parking in Newton

This is a duplex condo that can comfortably accommodate two families. The upper level has 2 bedrooms and 1.5 bathrooms, suitable for 2–4 guests. The lower level (basement) has 1 bedroom and 1 bathroom, also suitable for 2–4 guests. If you would like to use the basement space, please let us know in advance. The basement suite will be opened for group of 5 guests or more.

Top guest favourite
A modern living area is furnished with a sectional couch and a vibrant red chair. A large television is mounted on the wall above a dark wood entertainment unit, which holds decorative items. Wooden floors and recessed lighting contribute to a bright and welcoming environment.
Home in Watertown
4.96 out of 5 average rating, 137 reviews

Absolutely Gorgeous 3 Bedroom Close to Boston

Enjoy a stylish experience at this recently-renovated, modern 3-bedroom apartment. Centrally-located, modern, bright and located in a historic Boston suburb on a quiet, private-way with plenty of free, off-street parking and within walking distance to the town center, river walk, bike paths and dog park.

Guest favourite
A spacious deck features a rectangular dining table surrounded by six black metal chairs. Lush greenery and the serene lake are visible in the background, with a clear sky and scattered clouds above, creating an inviting outdoor space.
Home in Hudson
4.9 out of 5 average rating, 103 reviews

Lake home

Enjoy the lake view from the dining room, living room and bedroom! There is a deck with a BBQ, full kitchen, 1 bedroom and 1 bathroom. For 2 guests only please. No parties or gatherings allowed. The beach / dock will be shared the the tenant below. Use of kayaks, paddleboard and canoe is allowed.

Guest favourite
Home in Dedham
4.84 out of 5 average rating, 570 reviews

Private apartment close the city!

New couch! New towels and linens! Fresh paint! New flooring coming soon. This private apartment is part of my home but has a separate entrance, full bath, living room and private bedroom. We're in a family neighborhood close to the city, and very convenient for those visiting with a car.

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