Holiday rentals in Middlesex County

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Top-rated holiday rentals in Middlesex County

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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, 115 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
The exterior of a Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.
Flat in Newton
4.87 out of 5 average rating, 559 reviews

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

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, 103 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.

Guest favourite
A modern studio features a spacious queen bed situated near a window that allows natural light to fill the room. A soft grey sectional couch faces a mounted 65” SmartTV, while a decorative mirror and a potted plant add a touch of warmth.
Flat in Boston
4.89 out of 5 average rating, 65 reviews

Stylish studio with room divider near downtown

Experience Boston in this incredibly stylish studio. Comes with a room divider for 1 bedroom like feel! Just a 5 min walk from the T and close to Boston College/Harvard, you can engage with all of Boston tastefully. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed Ideal for business travelers, couples, nurses, those in hospital treatment and everyone looking to experience Boston in comfort and peace.

Guest favourite
The bedroom features a spacious bed adorned with navy bedding and accented by decorative pillows. Nightstands with lamps are positioned on either side. Natural light enters through a window, illuminating the warm wooden flooring.
Guest suite in Stow
4.98 out of 5 average rating, 112 reviews

Sisu Suite: Private one bedroom suite

Private suite with separate entrance. Locked door between suite and home. Sitting room with love seat, folding wall-mounted table/desk and chairs, tv, and kitchenette. Kitchenette includes mini fridge, microwave, coffeemaker, water kettle, and toaster. Bedroom with queen sized bed. New bathroom. 25 miles west of Boston. Minutes from pick-your-own apple orchards, winery, cider breweries, and golf courses. Backyard connects to conservation land trails. 3.3 miles from S. Acton Rail station.

Top guest favourite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 329 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

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
4.98 out of 5 average rating, 143 reviews

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)

Top guest favourite
A spacious loft area features a queen-sized bed with a cozy comforter and decorative pillows, alongside a daybed for seating or lounging. Wooden beams and a rustic brick hearth enhance the charm. Light enters through multiple windows, illuminating the inviting space.
Guest suite in Littleton
4.91 out of 5 average rating, 449 reviews

Historic Loft with bathroom & kitchenette

A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

Guest favourite
A stone patio overlooks the calm lake, featuring a fire pit surrounded by low seating and greenery. A wooden dock extends into the water, complementing the serene landscape. Lush trees frame the view, enhancing the natural setting.
Flat in Hudson
4.85 out of 5 average rating, 359 reviews

Private Mother-In-Law apartment on the lake!

Waterfront on the Lake with a private beach and dock. Relax on your deck and Patio with Wonderful Views. This is a mother-in-law private downstairs apartment complete with kitchen and separate entrance. Enjoy the lake with a fire pit and use of paddle boat and kayaks (life jackets provided). Enjoy the wonderful eclectic restaurants in downtown Hudson including a Micro Brewery, Pub, Martini Bar, Micro Creamery and even a SpeakEasy.

Superhost
A spacious living area features a dark gray futon adorned with patterned cushions, accompanied by a wooden coffee table. A rustic wooden cabinet houses a television, while natural light is invited through the glass doors leading to an exterior space.
Flat in Hudson
4.92 out of 5 average rating, 561 reviews

Newly Renovated Apartment Near Downtown Hudson

Newly renovated private attic apartment near downtown Hudson with kitchenette, living room and bedroom/office. A warm, cozy space with plenty of natural light! Just upgraded to a new king sized bed! Free parking on site Walking distance to restaurants, cleaners, antique shops, roller skating, shopping center, gym, breweries, golf course... & lots more! Nearby there are lots of historical sites, ski areas, and areas for swimming!

Top guest favourite
A charming guest house is shown with a welcoming wraparound porch, adorned with a striped awning. Lush green grass leads to the house, surrounded by trees and landscaped beds. A gravel path extends alongside, enhancing the outdoor space.
Barn in Acton
5 out of 5 average rating, 52 reviews

Hidden Gem

This memorable hidden gem in historical Acton, is anything but ordinary. With your own parking area and semi-private entrance this tastefully decorated guest house is close to many hot spots. The Bruce Freemen Rail Trail, Nara Park, Kimball’s farm in Westford and historical Concord just to name a few. Situated Thirty minutes west of Boston makes it easily accessible to all routes north, south, east and west.

Top guest favourite
Flat in Littleton
5 out of 5 average rating, 34 reviews

Country Retreat

About this place: This is the ideal location to explore the joys of New England particularly during our nation’s 250th anniversary. Although in a rural area the apartment is conveniently positioned at the junction of interstate 495 (North and South) and route 2 (East and West). Historic Concord is 5 minutes away, Lexington 10 minutes and just 25 minutes to Boston (depending on traffic).

Popular amenities for Middlesex County holiday rentals

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