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

4.91 out of 5 average rating, 127 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.

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Guest favorite

Guesthouse in Dorchester

4.89 out of 5 average rating, 153 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 and double deck family homes. This community has historic Victorian houses, access to pristine city beaches, the JFK Library and many historic interests.

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Top guest favorite

A cozy living area features a dark green sofa and a wooden coffee table atop a patterned area rug. A large window brightens the space, showcasing a dining table with four pink chairs. A ceiling fan provides airflow, complementing the relaxed atmosphere.

Guesthouse in Melrose

5.0 out of 5 average rating, 26 reviews

Spacious& Convenient 1BR unit-20min to Boston

Stay in a spacious and clean family-friendly place, just 20mins drive from Boston & the Logan airport. Enjoy all the city conveniences being few mins walk from Whole foods grocery store, downtown Melrose's great restaurants & coffee shops, CVS, gift stores, spa & the peaceful Ell pond. Steps from public transportation (bus), or quick drive to Oak Grove Station for direct subway train to Boston. Very close to Melrose Wakefield Hospital. Perfect for those who enjoy the quiet yet be near Boston.

LocationFamilyWalkability

Superhost

A welcoming living room features light-colored sofas adorned with decorative pillows. Natural light filters through two windows, illuminating a cozy atmosphere. A lamp and a dresser add functionality, while a neutral carpet completes the space. Greeting from the entrance can be seen in the background.

Guesthouse in Worcester

4.82 out of 5 average rating, 331 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.

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Top guest favorite

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

Guesthouse in West Roxbury

4.95 out of 5 average rating, 215 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

FamilyValueLong stay

Top guest favorite

A spacious front porch is adorned with cheerful yellow curtains and comfortable seating. Planters filled with vibrant flowers add a touch of color. An American flag gently waves in the breeze, complementing the peaceful outdoor setting.

Guesthouse in Melrose

4.99 out of 5 average rating, 155 reviews

Jimmy & Donny's AirBnB

2 level guesthouse! PRIVATE 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/KIDS OR SMOKING

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Superhost

The exterior of a historic two-story home is showcased, featuring a light-colored façade and multiple large windows. The entrance is marked by a welcoming door with a bright hue. Nearby, recycling and trash bins are visible, accompanied by landscaped trees in autumn colors.

Guesthouse in Holliston

4.71 out of 5 average rating, 24 reviews

2BR/2BA in a Duplex | Private Entry | Downtown

Suitable for family stays due to railroad bedroom setting. Beautifully restored 1850s home, 2-bed, 2-bath home. Downtown&Walkable. The home is close to Hopkinton, Framingham, Boston, Providence, and Worcester, with easy day trips to Cape Cod, Salem, North Shore beaches, and several ski areas. Gillette Stadium is about 25 minutes away for concerts and upcoming World Cup events, and you’re just 7 minutes from the starting line of the Boston Marathon in Hopkinton.

LocationFamilyHeating

Top guest favorite

A comfortable living area features a soft sectional sofa, a round coffee table with a woven basket, and a reptilian-patterned rug. Natural light enters through two large windows adorned with light curtains. A potted plant, floor lamp, and stylish accent chairs create an inviting ambiance.

Guesthouse in Maynard

4.98 out of 5 average rating, 55 reviews

Cozy Maynard duplex: 3BR with Wood stove

Welcome to the most walkable town in Metro Boston, w/ movie theater, live performance venue, beer garden, galleries, shops, & 17 restaurants 1/2mi from our front door. Our 1910 mill town company house is a little oasis. This is a two-family house; two separate private residences side-by-side. My family occupies the other side and seasonally rents it. Between house & garage, the outside dining area and fire pit are for your private use.

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Superhost

A spacious bedroom features a large bed adorned with a patterned green and white quilt. Natural light floods the room through multiple windows, highlighting a small desk and ergonomic chair. Soft lighting is provided by sconces on the walls.

Guesthouse in Worcester

4.82 out of 5 average rating, 109 reviews

Quiet Oasis In The City

Forget your worries in this spacious and serene space. We are right in the city but you'll feel miles away. This two level guest home is surrounded by nature and very relaxing. Two bedrooms and two baths. Two king sized beds. One full bath with oversized tub downstairs. Upstairs bath with standing shower. Full kitchen and coffee and tea. Hot tub is included with BNB. Pool is a separate rental. Message for details.

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Guest favorite

Guesthouse in Dedham

4.92 out of 5 average rating, 24 reviews

Slow Down| Your Boston Getaway

Private entrance, 6+ private parking spaces, and a large green outdoor area perfect for relaxing. Quiet family-friendly neighborhood. Features 2 spacious bedrooms with 3 queen beds, smart bathroom, modern kitchen, and smart self check-in with a unique code for each guest. Enjoy complimentary Colombian coffee plus starter essentials including toilet paper and cleaning supplies for a comfortable stay.

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Top guest favorite

Guesthouse in Framingham

5.0 out of 5 average rating, 16 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.

LocationFamilyGetting around

Top guest favorite

A leather recliner sofa is positioned in a light-filled living area, complemented by a large painting of a serene landscape. A full-size refrigerator and a TV stand are visible, providing essential amenities. An entryway is seen in the background, leading to additional rooms.

Guesthouse in Framingham

4.98 out of 5 average rating, 341 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.

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