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

Guesthouse in Andover

4.94 out of 5 average rating, 96 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.

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

4.82 out of 5 average rating, 274 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.

Top guest favorite

Guesthouse in Maynard

5 out of 5 average rating, 28 reviews

Cute mill house: 3BR•Wood stove *Brkfst included*

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. Between house & garage, the outside dining area and fire pit are for your private use. Beyond the garage, we invite you to share our backyard w/ pool and badminton.

Guest favorite

The entrance to the Windsor Carriage House is framed by a welcoming archway, featuring a decorative sign and potted flowers. A brick pathway leads to the door, with greenery lining the sides and glimpses of the neighboring structures visible in the background.

Guesthouse in Melrose

4.99 out of 5 average rating, 85 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, 102 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

4.88 out of 5 average rating, 113 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.

Top guest favorite

A cozy living area features a comfortable dark sectional sofa adorned with decorative pillows. A modern coffee table sits on a woven rug, while a television is positioned on a stylish stand. Natural light filters in through small windows, creating a warm ambiance.

Guesthouse in Arlington

5 out of 5 average rating, 8 reviews

The Cozy Current with A/C

Have fun at The Cozy Current! This charming one-bedroom offers easy access to the nature and nearby transit. Just 1-minutes walk to the bus stop and ten minutes to the Red Line, you'll be exploring Boston in no time. The spacious living room features pull-out sofa for extra guest, and the simple kitchenette is perfect for a quick meal. With A/C, a cozy vibe, and a prime location near cafes and bike paths, it's the idea spot for your vacation or business stay.

Top guest favorite

A covered porch features two comfortable chairs with striped cushions arranged next to a wicker side table. Large windows allow natural light to fill the space, while a ceiling fan provides ventilation. Lush greenery is visible beyond the railing, adding a serene touch.

Guesthouse in Norwood

5 out of 5 average rating, 14 reviews

Spacious Suite 15 mi from Boston

This spacious two bedroom one full bath guest unit is all yours to enjoy and call home for your visit. This unit has 2 entrances, parking for 1 car, and a large capacity Washer/Dryer. The house is nestled behind an old mansion. It is close to markets and the center of town. The Commuter Rail makes 2 stops in town and will take you into Boston in a ½ hour. Gillette Stadium, Home of The New England Patriots and the popular Shopping Center is 7 miles away.

Superhost

A well-equipped kitchen features light wood cabinetry and a neutral countertop. Appliances including a dishwasher, microwave, and stovetop are visible. Natural light filters in through nearby windows, illuminating the space and providing a welcoming atmosphere for meal preparation.

Guesthouse in Shrewsbury

4.73 out of 5 average rating, 228 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

A charming cottage is set among lush greenery, featuring a gravel pathway leading to the entrance. The exterior showcases a light gray color with multiple windows, surrounded by well-maintained grass and a few trees, creating an inviting and serene atmosphere.

Guesthouse in Framingham

5 out of 5 average rating, 12 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

A private wooden deck is accessible via a small set of steps, featuring a railing for safety. The area is bordered by a wooden fence, and lounge chairs are arranged for relaxation. Green grass and shrubs surround the deck, enhancing the natural setting.

Guesthouse in Framingham

4.97 out of 5 average rating, 281 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

The entrance features a black door adorned with a festive wreath, welcoming guests. A well-lit lantern hangs above, providing soft illumination. The pathway is bordered by a white picket fence, and greenery is visible in the background, creating a serene and inviting approach to the studio.

Guesthouse in Newton

4.93 out of 5 average rating, 114 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.