Guesthouse holiday rentals in North Shore

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Top-rated Guesthouses in North Shore

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite
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 Gloucester
4.96 out of 5 average rating, 302 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 favourite
A serene view of the calm lake is presented, framed by trees and surrounding greenery. The water reflects the clear sky, while homes are visible along the bank, creating a peaceful landscape perfect for relaxation.
Guesthouse in Salem
4.93 out of 5 average rating, 134 reviews

Lake Front Private Guest House in So. NH

Just 36 miles north of Boston/Logan Airport. Enjoy lake views from this above garage private entrance guest house. Two private bedrooms (1 queen/1 full) w/additional queen futon. Unit is clean & comfortable with 2 smart tv's, wifi, Keurig, microwave, minifridge/freezer. Explore lake using 2 available kayaks. Two public beaches nearby. Parking for 3 cars. Minutes from Canobie Lake Park, Tuscan Village & 5 popular wedding venues. Short drive to So Maine, NH seacoast, white mountains & foliage.

Top Guest favourite
A white picket fence frames the entrance, featuring a decorative planter with flowers. The welcoming front door is partially visible, situated beneath a classic porch light. Surrounding greenery adds a touch of nature to the charming exterior, gently illuminated in the evening light.
Guesthouse in Beverly
4.98 out of 5 average rating, 187 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 favourite
A hot tub is situated on a wooden deck, surrounded by greenery. A light green chair is placed near the hot tub, offering a relaxing spot to enjoy the outdoor space. The exterior wall of a building in the background features a bright turquoise color.
Guesthouse in Rockport
4.99 out of 5 average rating, 153 reviews

Gingerbread House | Hot Tub | 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!

Top Guest favourite
Guesthouse in Kingston
4.99 out of 5 average rating, 137 reviews

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.

Top Guest favourite
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
4.99 out of 5 average rating, 146 reviews

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

Guest favourite
Natural light fills the spacious living area, highlighting comfortable seating and a cozy nook with cushions. A wooden ladder leads to an elevated bookshelf and soft reading space. Large windows offer views of the maintained gardens outside.
Guesthouse in York
4.91 out of 5 average rating, 556 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 favourite
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
4.93 out of 5 average rating, 120 reviews

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.

Guest favourite
An open living space features a comfortable sofa and a round coffee table set atop a patterned area rug. Light floods through large windows dressed in colorful curtains, illuminating an adjoining kitchen with bar seating.
Guesthouse in Rockport
4.89 out of 5 average rating, 275 reviews

Beautiful Apartment Near Town & Beaches

Sunny one bedroom apartment with seasonal views! Fully equipped kitchen, open floor plan, balcony and everything to make your stay pleasant and comfortable. The apartment is on the second floor of a garage. Some noise may come from the garage between 9am and 5pm. We're 1.5 miles from the heart of town and beaches, a 20 minute walk along the ocean. Also about 1.5 miles from the train station. Parking on site, off street is available for 1 car only.

Superhost
An outdoor hot tub is situated on a wooden deck, surrounded by decorative screen panels for privacy. Sunlight reflects off the water's surface, and nearby, a wall-mounted coat hook can be seen alongside a gray chair. The setting is designed for relaxation.
Guesthouse in York
4.87 out of 5 average rating, 289 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.

Top Guest favourite
A modern kitchen is presented with white cabinetry and gray countertops. Essential appliances include a microwave, coffee maker, and dishwasher. A window allows natural light to brighten the space. A blue and white patterned mat lies on the floor near the sink.
Guesthouse in Hampton
4.88 out of 5 average rating, 171 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 favourite
Guesthouse in Framingham
4.98 out of 5 average rating, 333 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.

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