Guest house holiday rentals in Middlesex County

Find and book unique guest house rentals on Airbnb

Top-rated guest house rentals in Middlesex County

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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Guest favourite

Guest house in Boston

4.99 out of 5 average rating, 231 reviews

The Red Door Carriage House

The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.

27 Dec – 3 Jan

₹24,663 per night

Guest favourite

Guest house in Worcester

4.81 out of 5 average rating, 209 reviews

Carriage house apartment

We have a one bedroom apartment at our historic home, Liberty Farms, which is the 2nd oldest house in Worcester Massachusetts. Also well known as the Abby Kelley Foster house to the locals. The full kitchen has all of the amenities: stove, microwave, fridge, disposal and stack-able washer & dryer. Guests may enjoy the patio and grounds in the quiet Tatnuck Square area, conveniently located minutes from the Worcester Regional Airport, restaurants, and hiking trails. House tours upon request.

22–29 Mar

₹12,423 per night

Guest favourite

Guest house in Newton

4.99 out of 5 average rating, 68 reviews

Sunny 1BR w views, close to BC and Boston

Newly renovated and furnished one-bedroom apartment on second level of historic carriage house atop Heartbreak Hill, and mere steps to Boston College, shops, and easy access to Boston via public transportation (MBTA Green Line). Offers panoramic views of Boston skyline, Boston College campus, Chestnut Hill reservoir and stadium. Features newly renovated kitchen, private laundry, air conditioning and a private terrace. This apartment is professionally cleaned between visitors.

28 Sep – 5 Oct

₹37,811 per night

Guest favourite

Guest house in North Andover

4.97 out of 5 average rating, 186 reviews

Spacious Studio Guesthouse at Winery w/ Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

21–28 Dec

₹31,631 per night

Guest favourite

Guest house in Melrose

4.97 out of 5 average rating, 59 reviews

Jimmy & Donny's AirBnB

A modern, beautiful, 2 level guesthouse! private entrance, bedroom/bath/living area. Spacious porch & patio. Melrose is centrally located 7.5 miles north of Boston, 2 convenient train stops, 20 minutes away, into downtown Boston. A short walk to The Fells Reservation 4 hiking & kayaking, or visit the Stone Zoo. We have Italian/Seafood/Mexican/Spanish/Mediterranean & Revolutionary Style Tavern restaurants in Melrose. Owners always on property. NO PETS/NO KIDS.

27 Mar – 3 Apr

₹10,841 per night

Guest favourite

Guest house in Andover

4.94 out of 5 average rating, 72 reviews

Rose Cottage - Walk to Downtown Andover

Bright and charming free-standing cottage walking distance to downtown Andover. Quiet residential street. One bedroom with queen bed and tv. Full kitchen with two-seat high-top table. Small den with couch, desk, office chair, and tv. Bathroom had a shower stall. Private outdoor patio seating overlooking quiet woods. Walk to Phillips Andover, Merrimack College, and MBTA into Boston — come enjoy every this charming New England town has to offer!

30 Jul – 6 Aug

₹12,776 per night

Superhost

Guest house in Shrewsbury

4.71 out of 5 average rating, 196 reviews

A Comfy Hilltop Home

Nice and comfy home with spectacular views and sunset! This house overlooks the rolling Worcester hills for miles and miles. Convenient location, quiet neighborhood, big backyard, expansive deck, and nearby scenic hiking trails. The house has 2 bedrooms, 1 kitchen, 1 full bathroom, washer & dryer, big deck, and lots of parking space. Beautiful and comfortable, with everything you'd need for cooking and relaxing.

21–28 Jan

₹9,370 per night

Guest favourite

Guest house in Framingham

4.98 out of 5 average rating, 202 reviews

Private guest house on beautiful country road

Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

17–24 Apr

₹10,408 per night

Superhost

Guest house in Lexington

4.71 out of 5 average rating, 181 reviews

Unique Loft/ Studio Guesthouse (super convenient)

Unique, double-height loft / studio - with 1 queen bed, and one sleeping/pull-out couch; Super convenient to Lexington town center - 3 min walk to restaurants, Starbucks, all the historical attractions and buses to Alewife (last stop of subway to Boston). Minutes to Rt 2 and Hwy 95 for business travelers to get to other parts of metro Boston

15–22 Dec

₹9,690 per night

Guest favourite

Guest house in Westford

4.98 out of 5 average rating, 80 reviews

Detached Waterfront Guest House

Fully furnished and equipped rental in MA. This completely renovated detached private studio guesthouse is ideal with peaceful setting and your own private outdoor deck overlooking the pond. Located in the beautiful town of Westford MA. Just 35 to 40 min northwest of Boston and 10 minutes from the NH border. Five minutes to US Route 3.

17–24 Nov

₹10,072 per night

Guest favourite

Guest house in Bedford

4.95 out of 5 average rating, 22 reviews

Guest suite in Bedford

Stay in a private, bright, spacious, and relaxing guest suite in Bedford, MA. Close to historic Concord and Lexington. You will be renting the entire suite to yourselves with your own separate entrance away from ours. Whilst the guest suite is attached to the main property, there is no direct access between this and the guest suite.

15–20 Sep

₹12,758 per night

Superhost

Guest house in Watertown

4.8 out of 5 average rating, 132 reviews

Modern, Spacious, bright, private apartment

Newly renovated, modern design apartment with private entrance located in the center of Watertown. Just minutes away from public transportation to Harvard Square and Downtown Boston. Book stays of 31 days or more for discount. No parties or extra guests who are not on the reservation allowed in the unit.

10–17 Sep

₹16,700 per night