Guesthouse holiday rentals in Boston

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

Lake View New England Cottage in Hamilton, MA

The Cottage is in rural Hamilton on the North Shore, just 40 mins from Boston. The property is set in grounds beside Lake Chebacco, with lovely waterfront views of the lake. The Cottage is a tranquil retreat, just a few minutes drive away from Cranes Beach, Ipswich, Cape Ann and many beaches and walking trails. Both Gordon College and Gordon Conwell are under 10 minutes drive away. Popular Salem is just 20 minutes drive away. Off street parking for 1 car. No children <15 due to safety

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.

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.

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.

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.

(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.

Beautiful Cambridgeport Apartment (Central Square)

Modern apartment with a beautifully furnished bedroom (plus office area) and a separate living area with a comfortable couch with a television and a kitchenette (Breville toaster, microwave, Nespresso). Property is located in Cambridge between Charles River and Central Square as well as being centrally located between Harvard and MIT. This beautifully renovated apartment will give you privacy and peace in the heart of Cambridge for you and your family to enjoy!

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.

Adorable 1 bedroom guest house with ocean view

Take it easy at this unique and tranquil getaway with an amazing ocean view. Enjoy the oversized deck for sunning, and grilling. 1 Queen bedroom and a pull out sleeper sofa in the family room with TV and WiFi. Kitchen includes basic appliances: mini-fridge, microwave, Keurig, toaster, toaster oven, air fryer, and portable cooktop. Amenities include use of sand volleyball court, linens and towels, window A/C, water toys, and 1 parking spot.

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.

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