Guesthouse vacation rentals in Boston

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Top-rated guesthouse rentals in Boston

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Guest favorite

Guesthouse in Scituate

5 out of 5 average rating, 34 reviews

The Genkan • Scituate's Cozy Harbor Guesthouse

Welcome to the Genkan, a transformed haven that was once a welder's garage. Modern, spacious, and private with stunning woodland views. Ideal for two people (2 more guests permitted with a fee to setup cots). Walking distance to Scituate Harbor, yet serene. Unwind in the open layout, enjoy nature's tranquility through large windows. Comfortable sleeping arrangements and open layout. Each item carefully curated with its own story. A labor of love, The Genkan offers a unique Scituate retreat.

Guest favorite

Guesthouse in Beverly

4.98 out of 5 average rating, 149 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 Cohasset

4.99 out of 5 average rating, 73 reviews

Sparkling new guesthouse 5 min from downtown

Newly renovated studio apartment over two car garage with separate entrance and parking for up to 2 cars. Bright, quiet, and clean, the space features high ceilings, new carpeting and furniture, new king sized Casper mattress, a sizable bathroom with heated floors, large shower with bench, convenient kitchenette with mini fridge, microwave, and coffee maker. Ideal for guests of local weddings, New England tours, family visitors, or just a getaway, this rental is one of a kind!

Guest favorite

Guesthouse in Annisquam

4.94 out of 5 average rating, 62 reviews

Charming Guesthouse with Access to Private Beach

Private guest cottage in the village of Annisquam, just a 5-minute walk from private Lighthouse Beach. The guest house is separate but adjacent to the main house (which is also available for seasonal rental, including the cottage). Perfect for a couple seeking a quiet stay near friends or family. You will have 1 bedroom and 1 full bath with shower, and access to an outdoor shower. Dedicated onsite parking. The guest house has both heat and an air conditioning unit.

Guest favorite

Guesthouse in Cohasset

4.98 out of 5 average rating, 122 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 Marshfield

4.97 out of 5 average rating, 79 reviews

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.

Guest favorite

Guesthouse in Framingham

4.97 out of 5 average rating, 247 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.

Guest favorite

Guesthouse in Chestnut Hill

4.92 out of 5 average rating, 104 reviews

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.

Guest favorite

Guesthouse in Marblehead

4.92 out of 5 average rating, 229 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.

Guest favorite

Guesthouse in Scituate

4.98 out of 5 average rating, 110 reviews

Private Harbor Hideaway -walk Scituate to harbor!

Our Harbor Hideaway is located above the detached garage one block from Scituate's beautiful harbor shops, restaurants, and marina! Come enjoy our many beaches and relax in your private backyard! *Mini splits provide heat and A/C. *Cleanliness is a priority and have it professionally cleaned after each guest.

Superhost

Guesthouse in Watertown

4.79 out of 5 average rating, 142 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 West Roxbury

4.95 out of 5 average rating, 191 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.