Guesthouse holiday rentals in Boston

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.

Value · Family · Check-in

Cozy Guesthouse Near T-Station - Family Friendly

Welcome to your getaway home! You are sure to enjoy a wonderful experience in this newly renovated Guesthouse Studio, situated in Weymouth Landing. • Just a 5-minute walk to the Commuter Rail station for easy access to Boston and beyond. • Explore local stores, restaurants, and bars, all within walking distance. • Only 10 minutes away from South Shore Hospital. • A short 12-mile drive to Downtown Boston. Perfect for couples, small families, groups, business stays, and long-term rentals.

Value · Family · Comfort

Adorable 1-bedroom carriage house

Kick back and relax in this quaint refurbished carriage house, centrally located in Beverly, Massachusetts. The first floor offers a kitchen space (complete with a toaster oven and mini fridge) and a dining area, as well as a spacious living room set that is perfect for nights in after a day of exploring. If you prefer, the patio also has cozy outdoor seating! Upstairs, you can find a comfortable Queen-sized bed, a private bathroom, and a desk space that's perfect for working from home.

Value · Location · Wi-Fi

Cozy&Modern apt in South Peabody

This Cozy&Modern apt was completely renovated and freshly painted, thoughtfully designed for our guests when they come stay with us. We put a lot of love into every little detail. This apt is in the basement with big windows and plenty of natural lighting. It’s conveniently located close to popular spots such as Salem 4.5 miles and Boston 17 miles, Stop&Shop, Pharmacy and other amenities are just min away. This apt is located in a friendly neighborhood. We look forward to hosting you.

Location · Nearby · Long stay

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.

Family · Value · Parking

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

Value · Family · Hospitality

Cozy Private Loft, Easy Access to Boston

Welcome to your cozy, sunlit private loft—your perfect home away from home! This modern 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, downtown Melrose and Gillette. A comfortable, stylish home base to relax, recharge, and experience it all together.

Location · Family · Checkout

Salem/Beverly! Barn by the Harbor! August openings

Just discounted Aug. 18-27! I Perfect for getaways or coastal exploration. A last minute summer getaway! Minutes to Salem, steps to the harbor. Watch the boats while you sip coffee in bed! Enjoy the patio. Walk to downtown, beaches or commuter rail to Salem, Boston & Cape Ann. There is a lot to do on the North Shore and there is more to "sea" than Salem! I can give you great ideas! Fun local events happening everywhere! A few days and weeks open in Sept and October too.

Family · Location · Amenities

(3) New Garage Studio Guesthouse

Kick back and relax in our newly renovated studio guesthouse. Conveniently located in North Cambridge, walking distance to Davis Square. Features a beautiful bathroom, kitchenette with a two-burner induction stovetop, a Murphy bed, pull-out couch, and desk space for your convenience. All appliances and features are brand-new. We are long time Airbnb Hosts/Cambridge residents. We live in the house in front of the guesthouse and are available if you have any questions.

Location · Family · Cleanliness

Lovely 1 Bedroom Guest House. Downtown Cohasset

Lovely guest house. Newly renovated, nicely furnished & clean. Spacious living room/dining room with fully equipped kitchen. Large 1 bedroom & 2 full baths. Convenient location--walk to downtown, harbor, restaurants, churches and the Common. Train to Boston"s South Station 5 min away. Cohasset is the quintessential New England seaside village located on the South Shore of Massachusetts between Boston and Cape Cod. Host lives next door on property.

Family · Value · TV

Cozy Coastal King Suite | Steps to Beach & Town

Unplug in this private, standalone suite with ocean views in Marblehead. Walk steps to Devereux Beach or ride our complimentary bikes to Old Town’s best cafes, dining, and shops. Minutes from historic Salem! Features a luxury king bed, smart TV, dedicated workspace, full bath, cooler, and beach chairs. Enjoy total privacy, a reserved off-street parking spot, and 24/7 keyless check-in for the ultimate New England escape.

Value · Family · Cleanliness

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

Off-street parking, keyless entry, Wi-Fi, 2 BR + fold-out, 2.5 baths, lots of sunlight Steps from bus/subway, cafes and restaurants, the perfect base to celebrate a graduation, visit colleges or take in a game. 5-minute drive to Longwood Medical area. About 20 min to Fenway Park (car) or TD Garden (subway), Museum of Fine Arts (bus) or subway to Freedom Trail.

Value · Location · Kitchen