Guesthouse holiday rentals in Boston

4.89 out of 5 average rating, 154 reviews

Guesthouse in Dorchester

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.

4.96 out of 5 average rating, 103 reviews

A bright living space is displayed, featuring a brown sofa, a wooden coffee table, and a large area rug. Natural light streams through large windows, illuminating the open layout that includes a kitchenette with stainless steel appliances.

Guesthouse in Weymouth

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.

4.98 out of 5 average rating, 199 reviews

The entrance to the carriage house is framed by a welcoming black door, adorned with a seasonal wreath. Soft lighting from a lamp illuminates the pathway, while lush greenery and flowers create a serene atmosphere around the doorway.

Guesthouse in Beverly

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.

4.93 out of 5 average rating, 15 reviews

Guesthouse in Peabody

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.

Guesthouse in West Roxbury

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

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.

4.95 out of 5 average rating, 217 reviews

4.84 out of 5 average rating, 332 reviews

A charming outdoor patio area is showcased, featuring a glass-top table surrounded by six comfortable chairs. An umbrella provides shade, while lush greenery and colorful flower pots enhance the inviting space. The French doors of the barn are visible in the background.

Guesthouse in Beverly

Salem/Beverly! Barn by the Harbor! Sept. openings

Last minute openings 9/14-17 or 9/20-24 I Perfect for getaways or coastal exploration. An end of 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.

4.99 out of 5 average rating, 158 reviews

A spacious front porch is adorned with cheerful yellow curtains and comfortable seating. Planters filled with vibrant flowers add a touch of color. An American flag gently waves in the breeze, complementing the peaceful outdoor setting.

Guesthouse in Melrose

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

4.95 out of 5 average rating, 66 reviews

A modern kitchenette features a sleek white countertop and cabinetry against vibrant blue walls. Glass pendant lights in shades of red and black hang above a dining table set with plates and wine glasses. An array of appliances is organized for easy access.

Guesthouse in Cambridge

(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.

4.99 out of 5 average rating, 170 reviews

The living area features a light-colored sofa and matching armchairs, arranged around a central coffee table. A stylish rug anchors the space. Natural light is filtered through two windows, and decorative starfish are mounted on the wall, adding a coastal touch.

Guesthouse in Cohasset

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.

A broad view of a coastal landscape is presented, featuring expansive green fields that lead to the shoreline. The blue sky is dotted with soft white clouds, creating a serene backdrop. The calm ocean extends towards the horizon, inviting exploration and relaxation.

4.93 out of 5 average rating, 268 reviews

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.

Guesthouse in Jamaica Plain

A driveway paved with red bricks leads to a garage with black doors, situated at the front of a duplex building painted in soft yellow and accented with black trim. Bright sunlight illuminates the scene, highlighting the inviting exterior.

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.

4.91 out of 5 average rating, 79 reviews

5.0 out of 5 average rating, 13 reviews

Guesthouse in Cambridge

Cozy Riverside Cambridge Guesthouse & Parking Pass

Relax with the whole family at our peaceful guesthouse. It includes one bedroom with a full size bed, newly updated bathroom, as well as a shared back patio. Only 15 minutes on foot to Harvard or MIT and 7 minutes to the Central Square T stop, get to where you need to go with ease. Excellent WiFi for remote work. *Air conditioning recently added!*

Popular amenities for Boston guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.94 out of 5 average rating, 31 reviews

Guesthouse in Concord

Studio 1677 apartment in Concord, MA

A spacious oceanfront deck is visible, featuring a wooden bench and wrought iron chairs. The tranquil water and clear blue sky provide a scenic backdrop, while a colorful blanket is draped on a railing. Surrounding trees add a touch of greenery to the setting.

Anchorage Cottage

Guesthouse in Canton

RV-with-ME: World Cup Foxborough (Stationary RV)

Mordern Guest suit in Marblehead. 1 King Bed.

Guesthouse in Cambridge

Pristine Renovated West Cambridge Bungalow

Private room in Somerville

A cozy sleeping area is featured with a spacious bed adorned with a colorful quilt. Natural light filters through multiple windows, highlighting the wooden trim and a comfortable sofa nearby. A small side table and an antique cabinet add charm to the room.

Private room w/ private bath - single family house

4.94 out of 5 average rating, 262 reviews

Private room in Somerville

A cozy living area is furnished with a bright red futon sofa and a patterned area rug. A wooden ladder provides access to an upper level, while a bookshelf filled with books is seen in the background. A small coffee table sits in front of a mirror and a potted plant adds a touch of greenery.

Garden Retreat

4.95 out of 5 average rating, 124 reviews

Private room in Billerica

A cozy cabin interior features warm wooden paneling and a spacious bed draped in a bright red blanket. A central table with seating options is positioned near the bed, while a guitar rests nearby. Natural light enters through sliding glass doors adorned with blinds.

The Pool House at The Acropolis

4.95 out of 5 average rating, 111 reviews

Guesthouses with a patio

4.89 out of 5 average rating, 28 reviews

Guesthouse in Dedham

Slow Down| Your Boston Getaway

4.96 out of 5 average rating, 57 reviews

Guesthouse in Westwood

Private Suite•Gillette Stadium/Boston•BBQ•Parking

5.0 out of 5 average rating, 11 reviews

Guesthouse in Canton

2BR Convenient to Gillette Stadium and Boston

5.0 out of 5 average rating, 43 reviews

Guesthouse in Salem

Salem Waterfront Couples Retreat - 1 mi Downtown!

4.93 out of 5 average rating, 29 reviews

A spacious backyard is highlighted by a circular stone patio featuring six Adirondack chairs arranged around a fire pit. The well-maintained lawn surrounds the area, and a white wooden deck is visible in the background, leading to the entrance of the house.

Guesthouse in Wakefield

Cozy One Bedroom Private Unit - Prime Location!

5.0 out of 5 average rating, 35 reviews

A scenic view of the ocean at sunset is captured, featuring soft hues of orange and pink in the sky. A bench is positioned on the shoreline, while lush greenery and low bushes frame the foreground, creating a serene atmosphere.

Guesthouse in Scituate

Oceanview 2 bedroom 2 bath!

4.97 out of 5 average rating, 67 reviews

The Great Room features large windows that allow natural light to fill the space, revealing a blend of comfortable seating arrangements, including a black couch and a tufted mustard yellow sofa. A wooden coffee table sits center stage, complemented by a decorative rug and wall art.

Guesthouse in Scituate

The Genkan • Scituate's Cozy Harbor Guesthouse

5.0 out of 5 average rating, 58 reviews

An aquarium is featured in the background, housing colorful fish and aquatic plants, adding a lively element to the space. A light-grey sofa with decorative cushions sits in the foreground, complemented by a cozy ottoman. Natural light flows through a nearby window.

Guesthouse in Salem

The Fox Den

Guest house rentals with a washing machine and dryer

4.91 out of 5 average rating, 45 reviews

A spacious living area is furnished with a large sectional sofa and a wooden side table. Natural light filters through two windows adorned with sheer curtains. A light gray rug lays on the wooden floor, complemented by a wooden media console and decorative wall art.

Guesthouse in Norwood

Spacious Suite in a Central Location

5.0 out of 5 average rating, 27 reviews

A cozy living area features a dark green sofa and a wooden coffee table atop a patterned area rug. A large window brightens the space, showcasing a dining table with four pink chairs. A ceiling fan provides airflow, complementing the relaxed atmosphere.

Guesthouse in Melrose

Spacious& Convenient 1BR unit-20min to Boston

5.0 out of 5 average rating, 24 reviews

A spacious deck is shown with a contemporary dining table and chairs beneath a large umbrella. A grill is positioned nearby. The scene is complemented by a serene landscape of green fields and a sunset sky.

Guesthouse in Scituate

Stunning Views - Luxury Upgrades - Modern & Cozy

Superhost

Guesthouse in Dedham

Charles Chateau Guest House w/ King & Queen Beds

4.8 out of 5 average rating, 5 reviews

Superhost

The entrance features a pair of prominent wooden doors set within a white façade. Lush green plants and colorful foliage surround the doorway, creating a natural frame. A cobblestone pathway leads up to the entrance, providing a quaint approach to the cottage.

4.71 out of 5 average rating, 7 reviews

Marblehead Marina Bungalow-newly remodeled!

5.0 out of 5 average rating, 18 reviews

An open living space features a kitchen island with black granite countertops, complemented by white cabinetry. Arched windows allow natural light, highlighting the light wood flooring. A comfortable seating area with a couch and a work desk are visible, creating a multifaceted environment.

Guesthouse in Cohasset

2 Bedroom Guesthouse in Cohasset

4.94 out of 5 average rating, 47 reviews

A spacious kitchen and dining area is showcased with modern cabinetry and a wooden dining table surrounded by green upholstered chairs. Natural light is provided by a skylight and large windows, illuminating the open design and connecting indoor and outdoor views.

Guesthouse in Lincoln

Carriage house outside Cambridge