Guesthouse vacation rentals in Boston

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Boston

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Boston

4.99 out of 5 average rating, 234 reviews

The Red Door Carriage House

The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.

Guest favorite

Guesthouse in Beverly

4.98 out of 5 average rating, 113 reviews

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.

Guest favorite

Guesthouse in North Andover

4.97 out of 5 average rating, 188 reviews

Spacious Studio Guesthouse at Winery w/ Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

Guest favorite

Guesthouse in Melrose

4.97 out of 5 average rating, 61 reviews

Jimmy & Donny's AirBnB

A modern, beautiful, 2 level guesthouse! private entrance, bedroom/bath/living area. Spacious porch & patio. Melrose is centrally located 7.5 miles north of Boston, 2 convenient train stops, 20 minutes away, into downtown Boston. A short walk to The Fells Reservation 4 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/NO KIDS.

Guest favorite

Guesthouse in Cohasset

4.98 out of 5 average rating, 106 reviews

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.

Guest favorite

Guesthouse in Foxborough

4.96 out of 5 average rating, 104 reviews

Bates Boutique ☆ Home Away From Home

Stay at a recently renovated Bates Boutique specifically for your enjoyment. Highlights: - Fully redesigned kitchen & dining area - Relax in the living room with a 65" Smart TV (live channels, Netflix, Disney+, Hulu, Apple+, HBO Max, and others included) - Cozy bedrooms with heavenly bedding - 3 workspaces to ensure you can get work and play done - Outdoor patio & grill for fun inside & out

Guest favorite

Guesthouse in Framingham

4.98 out of 5 average rating, 205 reviews

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.

Superhost

Guesthouse in Braintree

4.73 out of 5 average rating, 30 reviews

The Pool House

Cute and quaint The Pool House has it all. A private stand alone building nestled between the main house and the pool includes a spacious 400 sq ft deck overlooking the pool. Interior updates include two new beds, all new bedding, countertops, vanity and more. The PH is conveniently located to all major highways and the Braintree Plaza. Dedicated parking.

Guest favorite

Guesthouse in Lexington

4.72 out of 5 average rating, 183 reviews

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

Guest favorite

Guesthouse in Marblehead

4.91 out of 5 average rating, 198 reviews

Devereux Beach Suite steps from beach

Enjoy beautiful views from second floor detached guest house with king bed and private entrance. Spend a day at Devereux Beach or stand up paddle board through the harbor, it's only steps away! We are a short walk to downtown shops, restaurants and bars. We have beach chairs, two bikes and a cooler for our guests.

Superhost

Guesthouse in Watertown

4.8 out of 5 average rating, 132 reviews

Modern, Spacious, bright, private apartment

Newly renovated, modern design apartment with private entrance located in the center of Watertown. Just minutes away from public transportation to Harvard Square and Downtown Boston. Book stays of 31 days or more for discount. No parties or extra guests who are not on the reservation allowed in the unit.

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 172 reviews

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. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.