Guesthouse vacation rentals in North Shore

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Top-rated guesthouse rentals in North Shore

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

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Top guest favorite

French doors open into a cozy living area where a sectional sofa is visible. A small green table with a bouquet of flowers sits in front, while sunlight illuminates the space. Outside, garden views reveal lounge chairs and vibrant flowers.

Guesthouse in Annisquam

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

4.97 out of 5 average rating, 315 reviews

Guest favorite

A cozy bedroom features a wooden bed with a light-colored duvet and decorative pillows. Natural light enters through the blinds, highlighting the warm wood flooring. A comfortable chair is positioned beside a lamp, and a subtle piece of wall art complements the tranquil atmosphere. A cooling unit is visible on the wall.

Guesthouse in Andover

The Rose Cottage *Walkable to Downtown Andover*

Welcome to your private retreat in the heart of Andover! This bright, charming cottage offers: *Prime Location: Walk to downtown shops, cafés & more! *Comfortable Stay: Cozy & clean 1 bdrm in a quiet area. *Outdoor Area: Enjoy outdoor seating surrounded by peaceful woods. *Ideal for Remote Work: Fast WiFi & dedicated workspace. *Full Kitchen: Cook meals & enjoy at a cozy two-person high-top table. *Forgot an essential? Enjoy a selection of toiletries/amenities to ensure your stay is worry-free.

4.91 out of 5 average rating, 128 reviews

Top guest favorite

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.

4.98 out of 5 average rating, 199 reviews

Top guest favorite

Guesthouse in Kingston

Accessory Apt on Wooded Property

Forget your worries in this spacious and serene space. Guest House/Over Garage Apartment tucked away on 6 acres. Centrally locataed in the seacoast region of New Hampshire. Close to mountains, beaches, hiking trails, lakes, & more. 15 minutes to Exeter, 30 minutes to North Hampton/Hampton Beach, 35 minutes to Southern Maine and Portsmouth, NH, 40 minutes to Manchester Boston Regional Airport, and 1 hour to Downtown Boston yet still tucked away in your own private retreat in the woods.

4.99 out of 5 average rating, 159 reviews

Guest favorite

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.

Guesthouse in West Roxbury

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

Top guest favorite

The historic carriage house is presented in a charming turquoise color, surrounded by lush greenery and flowering plants. Tall windows provide ample natural light. A spacious yard is visible, framed by a low stone wall and iron fence.

Guesthouse in Rockport

Historic Carriage House | Dog Friendly | Hot Tub

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!

4.99 out of 5 average rating, 169 reviews

Guest favorite

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.

4.84 out of 5 average rating, 332 reviews

Guest favorite

A quaint stone cottage is surrounded by lush greenery and colorful flowers, with a well-maintained garden featuring clusters of purple blooms. The cottage's rustic charm is complemented by a sloped lawn and mature trees, creating a serene outdoor atmosphere.

Guesthouse in Gloucester

Plum Cove Cottage with king suite!

A quaint 1900's cottage Plum Cove beach is just 500 ft away! The full gourmet kitchen has granite counters and stainless steel appliances. There is also a spa shower, romantic king bedroom with maple spiral stairs and 3 skylights which provide amazing light throughout. Watch the spectacular sunsets voted one of the best in the world by National Geographic. This is the premier location to begin your exploration of Cape Ann. Beach umbrellas and chairs provided.

4.94 out of 5 average rating, 124 reviews

Top guest favorite

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.

Guesthouse in Marblehead

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.

4.93 out of 5 average rating, 268 reviews

Top guest favorite

A leather recliner sofa is positioned in a light-filled living area, complemented by a large painting of a serene landscape. A full-size refrigerator and a TV stand are visible, providing essential amenities. An entryway is seen in the background, leading to additional rooms.

Guesthouse in Framingham

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.

4.98 out of 5 average rating, 342 reviews

Guest favorite

The exterior of the Tree Haus is captured, showcasing its distinctive red siding and contemporary architectural design. A welcoming entrance is flanked by well-maintained greenery, including small trees and shrubs. Soft natural light highlights the inviting atmosphere of the surrounding landscape.

Guesthouse in York

The Tree Haus in York Heights

Nestled in York Heights, just 1 mi from Long Sands Beach, our stylish retreat is centrally located to all southern Maine has to offer! Whether you are seeking breathtaking views of the iconic Nubble Lighthouse, enjoying the seaside while working remotely, or in need of a relaxing stopover on your way Down East, we welcome you to the Tree Haus.

4.96 out of 5 average rating, 102 reviews

Guest favorite

The image displays a modern, two-story home with a brown exterior featuring horizontal siding. A unique sculpture is situated on the front lawn, surrounded by landscaped greenery. A stone pathway leads to the entrance, which is framed by tall trees and shrubs.

Guesthouse in Lexington

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

4.74 out of 5 average rating, 272 reviews