Guesthouse holiday rentals in Middlesex County

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.

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/KIDS OR SMOKING

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.

Cozy Maynard duplex: 3BR•Wood stove•kid friendly

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.

Sunny Standalone Private Loft w/ Full Kitchenette

Welcome to your cozy, sunlit private loft—your perfect home away from home! This modern (b. 2024) flexible Boston retreat features a private entrance, kitchenette, chic full bathroom, dedicated office area, gardens, and a comfy queen bed plus a joybird sofa bed for additional guests. Enjoy a peaceful morning Nespresso located just a few steps to the commuter rail, restaurants, and downtown Melrose. Quiet, private, and beautifully styled—ideal for solo travelers, couples, or small families.

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.

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.

New Private Apartment

Enjoy your privacy and comfort in this calm, meticulously created walkout guest suite. Featuring a completely separate entrance, a full bathroom, queen bed, a well equipped kitchenette, and all the basic amenities to allow you to unwind in a clean, minimal aesthetic. With easy access to local hospitals, highways, shops, and restaurants, it's a perfect central location for any of your travels.

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.

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

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.