
Guesthouse vacation rentals in Middlesex County
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Top-rated guesthouse rentals in Middlesex County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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.

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.

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.

Luxury Spacious 2BR • King & Queen Beds • 2 Baths
Family-Friendly 2BR Getaway! Spacious stay with a 🛏️ King & Queen bed, ☀️ outdoor patio, 👶 baby crib! 🐶 pet-friendly neighborhood! Great for 🩺 travel nurses & 💼 professionals with ⚡ high-speed WiFi, 📺 Roku TV & 🎬 Netflix. Easy access to UMASS and St Vincent Hospitals 🏥 for work or care for loved ones. Close to 👵 Southgate Shrewsbury—perfect for visiting Grandma & Grandpa! Close to beautiful Dean Park—perfect for walks, playtime, or just soaking up nature. We’d love to host you!

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.

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.

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

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.

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.

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.

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.

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.
Popular amenities for Middlesex County guesthouse rentals
Family-friendly guest house rentals

(3) New Garage Studio Guesthouse

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

New Private Apartment

Cozy Private Loft, Easy Access to Boston

City Garden Level Studio

Modern, Spacious, bright, private apartment

Studio 1677 apartment in Concord, MA

Winn Efficiency/studio
Guest house rentals with a patio

Private Suite•Gillette Stadium/Boston•BBQ•Parking

Cozy One Bedroom Private Unit - Prime Location!

2BR Convenient to Gillette Stadium and Boston

Cozy Riverside Cambridge Guesthouse & Parking Pass

Northern Suburb

Private Guesthouse • 1BR/1BA • Quiet & Comfortable

Four Oaks Guest House Golf, UMass Lowell, 93/3/495

Dream Inn LLC Rm2 Fitchburg Free WiFi & Parking
Guest house rentals with a washer and dryer

Spacious Suite in a Central Location

Charles Chateau Guest House w/ King & Queen Beds

Carriage house outside Cambridge

Airy new apt for 2-6. Near subway. Free parking.

Charming 1880 Historic Carriage House

The Carriage House

Beautiful Cambridgeport Apartment (Central Square)

Private Studio Guest House w/ Free Parking
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- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Boston Common
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- Gillette Stadium
- Revere Beach
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- Canobie Lake Park
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