Guesthouse vacation rentals in Middlesex County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Middlesex County

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

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Guest favorite

A cozy bedroom features a wooden bed with a light-colored duvet and decorative pillows. Natural light enters through the blinds, highlighting the warm wood flooring. A comfortable chair is positioned beside a lamp, and a subtle piece of wall art complements the tranquil atmosphere. A cooling unit is visible on the wall.

Guesthouse in Andover

4.93 out of 5 average rating, 92 reviews

The Rose Cottage *Walkable to Downtown Andover*

Welcome to your private retreat in the heart of Andover! This bright, charming cottage offers: *Prime Location: Walk to downtown shops, cafés & more! *Comfortable Stay: Cozy & clean 1 bdrm in a quiet area. *Outdoor Area: Enjoy outdoor seating surrounded by peaceful woods. *Ideal for Remote Work: Fast WiFi & dedicated workspace. *Full Kitchen: Cook meals & enjoy at a cozy two-person high-top table. *Forgot an essential? Enjoy a selection of toiletries/amenities to ensure your stay is worry-free.

Superhost

The spacious master bedroom features a wooden dresser and a cozy chair paired with an ottoman. Natural light is allowed in through two skylights, illuminating the light-toned wooden floor and enhancing the neutral color palette of the room.

Guesthouse in Cambridge

4.89 out of 5 average rating, 38 reviews

Beautiful Cambridgeport Apartment (Central Square)

Modern apartment with a beautifully furnished master bedroom and office area (wifi). There is also a comfortable couch in the family area with an office desk, a television and a kitchenette (Breville toaster, microwave, Nespresso). Property is located in Cambridge between Charles River and Central Square as well as being centrally located between Harvard and MIT. This beautifully renovated apartment will give you privacy and peace in the heart of Cambridge for you and your family to enjoy!

Guest favorite

An outdoor seating area is featured on a wooden deck, showcasing a light-colored sectional sofa with cushions and a matching coffee table. A grill stands nearby, surrounded by greenery, while a welcoming area rug anchors the space. Sunlight illuminates the deck, highlighting its wooden texture.

Guesthouse in Worcester

4.81 out of 5 average rating, 262 reviews

Carriage house apartment

We have a one bedroom apartment at our historic home, Liberty Farm, which is the 2nd oldest house in Worcester Massachusetts and known as the Abby Kelley Foster house to the locals. Recent furniture upgrade in living room, see pictures. Kitchen has all of the amenities: stove, microwave, fridge, disposal and stack-able washer/dryer. Guests may enjoy the grounds in the quiet Tatnuck Square neighborhood, minutes from the Worcester Airport, restaurants, and hiking. House tours upon request.

Guest favorite

The exterior of the Carriage House is shown, featuring a distinctive shingled design and a dark door. A staircase leads up to the entrance, surrounded by a paved pathway and greenery.

Guesthouse in Melrose

4.99 out of 5 average rating, 81 reviews

Modern, Cute 2 BR Carriage House North of Boston

Private, two-floor Carriage House in quiet neighborhood near Melrose's downtown and public transportation to Boston (Orange Line and Commuter Rail within 1 mile). Large second floor has a king bed with a side bedroom more sleepers and updated bathroom. Fully-stocked with dishes, cooking ware, and supplies, the kitchen and laundry are on the first floor with a large couch and dining table for 6. We hope you feel like family when you’re here. Please be mindful this is our home, not a hotel.

Top guest favorite

A welcoming porch area is featured, with a round dining table under a large umbrella, surrounded by colorful planters. Two rocking chairs are positioned nearby, while soft lighting adds warmth to the inviting space.

Guesthouse in Melrose

4.98 out of 5 average rating, 94 reviews

Jimmy & Donny's AirBnB

Beautiful, 2 level guesthouse! Private entrance, bedroom/bath/living area. NOTE: BEDROOM/BATHROOM ON SECOND FLOOR UP SPIRAL STAIRCASE. Large porch. Melrose is located 7.5 miles north of Boston, 2 convenient train stops, 20 minutes away, into downtown Boston. A short walk to The Fells Reservation, 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.

Guest favorite

A compact bathroom features a white vanity with a sink under a framed mirror. Artwork lines the walls, adding character. Soft towels are neatly arranged on a small shelf, while blue tiles give the floor a refreshing touch. Natural light filters through a window with horizontal blinds.

Guesthouse in Boston

4.87 out of 5 average rating, 107 reviews

Prime City Location: Private Suite-separate entry.

This quiet residential neighborhood has easy access to a transportation hub (subway/bus/trolley/taxi), is 7 miles from the airport and has restaurants and services nearby - many within easy walking distance. My Codman Hill neighborhood is a premium area and represents the best of suburbia in the city. The neighborhood hosts primarily single family homes with double and triple deckers but the huge Victorian houses dating back to the 1700 and 1800's are within this community.

Superhost

An expansive deck is equipped with various seating options, including four reclining chairs, a table and chairs set, and a pair of colorful accent chairs. Lush greenery surrounds the area, providing a serene atmosphere with stunning views of the distant hills.

Guesthouse in Shrewsbury

4.73 out of 5 average rating, 225 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.

Top guest favorite

The entrance to the studio guest house is highlighted by green siding and white trim. A welcoming door with a decorative glass insert sits beneath a gently striped awning. Lush hostas and decorative stones line the walkway, enhancing the outdoor space.

Guesthouse in Boston

4.92 out of 5 average rating, 36 reviews

Private Studio Guest House w/ Free Parking

Detached Studio Guest House with FREE off-street parking, in the rear of owner-occupied main home. Located on a quiet street in a vibrant neighborhood in the City of Boston. Ideal for solo travelers or couples! • 15 mins from Logan Airport & Downtown. • Steps away from MBTA Red Line. • Nearby Restaurants, Cafes, Markets, Local Parks/Playgrounds, UMASS Boston, JFK Museum, Carson Beach, Castle Island.

Top guest favorite

A screened porch offers a serene view of the surrounding landscape, with a turquoise swing positioned for relaxation. Natural light brightens the space, enhanced by the blue ceiling and wooden flooring.

Guesthouse in Framingham

5 out of 5 average rating, 11 reviews

Enchanted Cottage on 5 Acres

Keep it simple at this peaceful and centrally-located place, a unique guest cottage located in a picturesque field. You won't believe it until you see it! the perfect little dream house that feels like being in the English countryside. Comfortably decorated and offers a fully equipped kitchen to meet your needs. There are two bedrooms upstairs and a full bath on each floor.

Top guest favorite

An outdoor seating area is surrounded by trees, featuring a stone fireplace with a cozy ambiance. A round table is paired with four metal chairs, each with red cushions, and is shaded by a large red umbrella. A small shed with a red door is visible in the background.

Guesthouse in Framingham

4.97 out of 5 average rating, 273 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.

Guest favorite

A spacious studio features vaulted ceilings and natural light from multiple skylights. The kitchenette is equipped with sleek cabinetry, and a wooden dining table with blue chairs is centrally located. A cozy seating area includes dark furniture and tasteful decor, inviting relaxation.

Guesthouse in Newton

4.93 out of 5 average rating, 110 reviews

Private Carriage House near Newton Center and BC

Large studio above garage with private entrance located on famous Heartbreak Hill. Kitchenette with Fridge, Microwave, Keurig and full bathroom. Less than 1 mile to Boston College and just minutes to Cambridge and Boston. Easy walk to public transportation and Newton Center with great restaurants, bars, parks, and shopping. Free off-street parking.

Top guest favorite

An outdoor seating area is visible, featuring a wooden table with foldable chairs. Flower pots with vibrant blooms add color to the entrance. A grill is positioned nearby, complementing the simple, welcoming exterior of the guest suite.

Guesthouse in Bedford

4.98 out of 5 average rating, 40 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.