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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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An inviting entrance features a decorative archway with birds perched atop. Stone steps lead to a charming cottage adorned with lush greenery and colorful flowers. Flagpole with an American flag stands nearby, creating a welcoming atmosphere.

Guesthouse in Gloucester

4.97 out of 5 average rating, 262 reviews

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

Top guest favorite

The exterior of a classic two-story farmhouse is displayed, featuring white siding and a welcoming front entrance. Seasonal decorations, including pumpkins, are arranged on the steps, while lush greenery surrounds the property against a backdrop of a blue sky with scattered clouds.

Guesthouse in Amesbury

4.95 out of 5 average rating, 122 reviews

Two Penny Loft at Amesbury Farmhouse - Guest Suite

This cozy 2 story guest suite w/separate entrance and deck, is part of a large 200 year old Amesbury farmhouse set on a peaceful 3 acre lot. The first floor contains a comfortable living/dining area, along with small charming bathroom. Upstairs is a large bedroom with vaulted ceiling, skylights, king-sized bed and sitting area. Amesbury is steeped in history and guests will be close to amazing breweries, restaurants, historical sites, shops, galleries, walking trails, lakes, beaches and more!

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

4.98 out of 5 average rating, 153 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.

Top guest favorite

A serene beach scene is featured, with calm waters reflecting a clear sky. Smooth stones border the sandy shore, while a gazebo can be seen on a rocky outcrop in the distance, providing a picturesque vantage point of the surrounding landscape.

Guesthouse in Rockport

4.99 out of 5 average rating, 103 reviews

Carriage House | Steps to Beach| Dog Friendly

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, full kitchen, queen sized bed with en-suite bathroom and a sun room that converts to an extra sleeping space perfect for kids. A 5 minute walk to the train for day trips to Salem, Gloucester, and Boston!

An elevated sleeping area is seen above a cozy nook, featuring a wooden bookcase filled with various books. Light streams in through large windows, illuminating the space. A small round table with a pair of cushioned seats offers a welcoming spot for relaxation.

Guesthouse in York

4.92 out of 5 average rating, 483 reviews

Stone Cove Cottage

Fall asleep to the sound of the York Harbor bell buoy and waves crashing on the shore. Awake to beautiful sunrises over the ocean and lobster boats heading out to sea. Walk to York Harbor Beach or stroll the Cliff Walk taking in quintessential Maine views. Long Sands Beach is a 3 minute drive and Short Sands and Cape Neddick Beaches just a bit further around the corner. The cottage sits on a shared property that boasts beautiful gardens and year round ocean views.

Top guest favorite

A welcoming private entrance features a wooden deck with a mat leading to a closed door. Flanked by vertical white pillars, the entrance is surrounded by well-maintained grass and mature trees, providing a glimpse of the lush outdoor space beyond.

Guesthouse in Portsmouth

4.98 out of 5 average rating, 146 reviews

Modern, Garden Level Studio Unit

A new and modern garden level studio with private entrance and free parking. My studio unit is conveniently located (1.5 MILES) to historic downtown Portsmouth and all it’s attractions and eateries. Plus, an even closer walk to the newest hot spot, the West End, boasting several local breweries like Great Rhythm, Liars Bench and restaurants such as Cornerstone Artisanal Pizza, the Kitchen, and Botanica.

Top guest favorite

A rustic sign marks the entrance to the College Woods Natural Area, surrounded by tall trees and a carpet of leaves. A dirt path winds through the serene woodland, inviting exploration into the lush greenery and tranquil atmosphere.

Guesthouse in Durham

4.99 out of 5 average rating, 167 reviews

"Oyster River Flat" new construction, walk to town

Enjoy our cozy guest flat on the same 1-acre property as our 1917 home, but with its own entrance, parking, full kitchen and bath. Walking distance to downtown Durham, the Oyster River, and Great Bay, with many hiking trails a short drive away. Take a walk to the historic Mill Pond Dam or to Tideline Public House (food truck park). This efficient space is for 1-2 people, with one queen bed available.

A rustic cabin is nestled among lush greenery, showcasing a stone patio with comfortable seating around a firepit. The outdoor area is surrounded by trees, enhancing the tranquil atmosphere, and features stepping stones leading to the entrance of the cabin.

Guesthouse in York

4.88 out of 5 average rating, 251 reviews

Cozy Cabin with hot tub, walk to beach, rock cove

Guest cabin in a private setting down a private road with short walk to Cape Neddick Beach and a secluded pebble beach. Guests have exclusive use of the firepit, outdoor sitting area and hot tub. The cozy and rustic post and beam cabin has two levels with a ladder to the loft level. Private and romantic for a couple, fun for a couple and one or two kids or just two adults.

A cottage exterior is visible with a covered porch featuring two chairs and a small table. A decorative wheel is mounted on the wall, while a clean driveway leads to the entrance. Nearby, various outdoor items are organized against the fence.

Guesthouse in Hampton

4.88 out of 5 average rating, 163 reviews

Cute Beach Cottage

Our updated cottage is located steps from the Beach, Boardwalk and beach activities. Quiet, safe street, AC, Smart TV, WIFI, Deck, BBQ grill. Why stay in a hotel room when you can vacation in our cozy cottage by the sea ! Nice updated kitchen. new paint and very clean. The boardwalk has many restaurants music, casino, gift shops Fireworks on Wednesday’s

Top guest favorite

A well-lit bedroom features a spacious bed with a light grey quilt. Bookshelves are positioned beside the bed, and sunlight filters through a partially open door leading to the living area. A soft rug is placed beneath the bed, adding warmth to the space.

Guesthouse in Framingham

4.97 out of 5 average rating, 273 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.

A private outdoor deck is set against a serene pond, surrounded by lush greenery and trees. A pathway of stepping stones leads from the deck to the water's edge, inviting guests to enjoy the peaceful natural surroundings.

Guesthouse in Westford

4.97 out of 5 average rating, 101 reviews

Detached Waterfront Guest House

Fully furnished and equipped rental in MA. This completely renovated detached private studio guesthouse is ideal with peaceful setting and your own private outdoor deck overlooking the pond. Located in the beautiful town of Westford MA. Just 35 to 40 min northwest of Boston and 10 minutes from the NH border. Five minutes to US Route 3.

Top guest favorite

An expansive view of a calm harbor is filled with numerous boats of various sizes, floating gently on the water’s surface. The scene captures the tranquility of the area, reflecting the sky's colors as the day transitions into evening.

Guesthouse in Lakeside Marblehead

4.91 out of 5 average rating, 234 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.

Vacation rentals for every style

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Cottages

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A space thats all yours, with room for everyone

Popular amenities for North Shore guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A shared yard is shown, featuring a grassy area surrounded by trees and plants. A small circular table with four chairs is positioned in the center, inviting relaxation amidst the greenery. The exterior of the surrounding houses is visible, adding charm to the peaceful setting.

Private room in Somerville

4.95 out of 5 average rating, 222 reviews

Private room w/ private bath - single family house

An open living space features a comfortable sofa, a coffee table, and a twin bed with a white bedspread. Large windows allow natural light to fill the room. A dining table is visible in the adjacent area, enhancing the inviting layout.

Guesthouse in Windham

4.85 out of 5 average rating, 82 reviews

Private Guest House

Top guest favorite

A spacious bedroom features a striped bedspread resting on a comfortable bed. Two bedside lamps provide soft lighting, and a cozy seating area is situated alongside a window fitted with a skylight. Light blue walls complement the room's serene atmosphere.

Guesthouse in Salem

4.97 out of 5 average rating, 76 reviews

Spacious 3 bedroom Suite Sleeps 6-8. 4 Beds

A white picket fence with a gate opens to a scenic view of the lake, surrounded by greenery. Flower pots are hung on the fence, adding color to the natural landscape. The calm water reflects the clear blue sky, enhancing the tranquil setting.

Guesthouse in Northwood

4.84 out of 5 average rating, 57 reviews

Lake Front, Beautiful, Private Studio w/Kayaks

Guesthouse in Boston

4.88 out of 5 average rating, 60 reviews

Airy new apt for 2-6. Near subway. Free parking.

Guest house rentals with a patio

Top guest favorite

A cozy bedroom is presented with warm wooden walls and ceiling. A spacious bed is adorned with a colorful blanket, complemented by decorative pillows. Natural light filters in through several windows, offering views of the surrounding greenery. A door leads to an outdoor area.

Guesthouse in Gloucester

4.94 out of 5 average rating, 66 reviews

Charming Guesthouse with Access to Private Beach

Top guest favorite

The exterior of a coastal cottage is displayed, featuring light-colored shingle siding and a welcoming white deck with railings. Sunlight reflects off the front, creating a bright atmosphere. The landscape includes grass and decorative stone accents, with a glimpse of the water visible in the background.

Guesthouse in Marshfield

4.98 out of 5 average rating, 82 reviews

Adorable 1 bedroom guest house with ocean view

Top guest favorite

Guesthouse in Melrose

4.98 out of 5 average rating, 94 reviews

Jimmy & Donny's AirBnB

Top guest favorite

The kitchen area features modern appliances, including a stove and refrigerator, with stylish cabinetry and open shelving holding decorative items. A wooden dining table is complemented by two upholstered chairs. Natural light enhances the space, creating an inviting atmosphere.

Guesthouse in Concord

5 out of 5 average rating, 26 reviews

The Groveside Guest House

The exterior of the cottage features a welcoming entrance with a light blue door framed by dark shutters. A mixture of shrubs and greenery adorns the front yard, complemented by seasonal decorations such as pumpkins. Soft lighting is provided by a hanging fixture on the porch.

Guesthouse in Cohasset

5 out of 5 average rating, 5 reviews

Cozy Cottage & Private Beach

Top guest favorite

A picturesque backyard features a well-maintained lawn bordered by trees and flower beds. Seating areas are arranged on a wooden deck, overlooking a serene water view. Paths lead through the garden, creating a tranquil outdoor space for relaxation.

Guesthouse in Portsmouth

4.97 out of 5 average rating, 58 reviews

Heron's Nest on North Mill Pond

A modern living area features a black sectional sofa adorned with decorative pillows, complemented by a stylish coffee table with green accents. The space is illuminated by recessed lighting, with warm orange curtains framing the windows and artwork displayed on the walls.

Guesthouse in Malden

4.83 out of 5 average rating, 65 reviews

Northern Suburb

Top guest favorite

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

5 out of 5 average rating, 37 reviews

The Genkan • Scituate's Cozy Harbor Guesthouse

Guest house rentals with a washer and dryer

Top guest favorite

The exterior of a cozy carriage house is displayed, featuring warm wooden siding. A small set of white stairs leads to the main entrance, flanked by trees and lush greenery. Two white Adirondack chairs are positioned on the manicured lawn, inviting relaxation.

Guesthouse in Dover

5 out of 5 average rating, 74 reviews

Luxury Guest House on quiet 4 Acre property

Top guest favorite

The entrance to the studio guest house is highlighted by green siding and white trim. A welcoming door with a decorative glass insert sits beneath a gently striped awning. Lush hostas and decorative stones line the walkway, enhancing the outdoor space.

Guesthouse in Boston

4.92 out of 5 average rating, 37 reviews

Private Studio Guest House w/ Free Parking

Top guest favorite

A fenced basketball court is visible, surrounded by greenery. The court features a standard layout with painted lines and a hoop at one end. Trees and shrubs border the space, providing a natural setting.

Guesthouse in Dunbarton

5 out of 5 average rating, 99 reviews

Bear Brook Trail Side Getaway & RV Park

Top guest favorite

Guesthouse in Maynard

5 out of 5 average rating, 27 reviews

Cute mill house: 3BR•Wood stove *Brkfst included*

Top guest favorite

A screened porch offers a serene view of the surrounding landscape, with a turquoise swing positioned for relaxation. Natural light brightens the space, enhanced by the blue ceiling and wooden flooring.

Guesthouse in Framingham

5 out of 5 average rating, 11 reviews

Enchanted Cottage on 5 Acres

Top guest favorite

The kitchen features modern white cabinetry, stainless steel appliances, and a well-organized countertop. A dining table is set with tableware, and natural light enters through the window, illuminating the space. The adjacent area includes a doorway leading to a dining space with black chairs.

Guesthouse in Abington

5 out of 5 average rating, 108 reviews

Cozy In-Law Apartment

A covered porch features two comfortable chairs with striped cushions arranged next to a wicker side table. Large windows allow natural light to fill the space, while a ceiling fan provides ventilation. Lush greenery is visible beyond the railing, adding a serene touch.

Guesthouse in Norwood

5 out of 5 average rating, 10 reviews

Spacious Suite 15 mi from Boston

The exterior of the Carriage House is shown, featuring a distinctive shingled design and a dark door. A staircase leads up to the entrance, surrounded by a paved pathway and greenery.

Guesthouse in Melrose

4.99 out of 5 average rating, 81 reviews

Modern, Cute 2 BR Carriage House North of Boston

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