Guest house 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.

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 outside Cambridge

On a converted educational farm, this recently renovated carriage house is perfect for a couple or young family. It is quiet, rural setting, but has easy access to Boston / Cambridge. There is a large yard / garden, which backs up onto conservation land and hiking trails. There is also a barn on the property with goats and chickens. Only a short drive to shops and restaurants in Lexington and Concord, as well as historical attractions like Walden Pond, Lexington Green, and Concord Museum.

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 also has historic Victorian houses dating back to the 1700 and 1800's .

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 and available for use until late October. Pool is a separate rental and closed for the season.

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. Between house & garage, the outside dining area and fire pit are for your private use.

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.

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