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

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

4.94 out of 5 average rating, 106 reviews

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.

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 Gloucester

4.96 out of 5 average rating, 283 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

Guest favorite

The exterior of the cottage is shown, featuring grey siding and white trim. A set of steps leads to the entrance, with a railing and a shaded porch. Colorful flowers frame the front yard, enhancing the welcoming appearance of the property.

Guesthouse in Hamilton

4.87 out of 5 average rating, 223 reviews

Lake View New England Cottage in Hamilton, MA

The Cottage is in rural Hamilton on the North Shore, just 40 mins from Boston. The property is set in grounds beside Lake Chebacco, with lovely waterfront views of the lake. The Cottage is a tranquil retreat, just a few minutes drive away from Cranes Beach, Ipswich, Cape Ann and many beaches and walking trails. Both Gordon College and Gordon Conwell are under 10 minutes drive away. Popular Salem is just 20 minutes drive away. Off street parking for 1 car. No children <15 due to safety

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, 170 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

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

4.99 out of 5 average rating, 137 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 favorite

A cozy living area features a dark upholstered couch and wooden dining furniture set for four. Natural light enters through a skylight and a window, illuminating the space. A patterned rug lies beneath a coffee table surrounded by books and games, enhancing the inviting atmosphere.

Guesthouse in Dunbarton

5 out of 5 average rating, 134 reviews

Bear Brook Trail Side Getaway & RV Park

Come stay in our peaceful one bedroom black bear themed unit. Cozy living room with games, smart tv, wifi, dvd player and movies. Great work space in bedroom. Unit has a full kitchen, full bath. Enjoy axe throwing, shoot some hoops or sit by the campfire (pending fire bans in drought conditions.) Hike to the brook and enjoy our trails on 15 acres. Check out our guidebook for ideas on tons of local dinning and activities. Min from Hopkinton/Everett trail system and Clough state park.

Top guest favorite

The spacious living area features high ceilings and natural light streaming through large windows. A comfortable sectional couch is arranged around a wooden coffee table, with two accent chairs positioned nearby. A television is mounted on the wall, contributing to the cozy atmosphere.

Guesthouse in Kingston

4.99 out of 5 average rating, 108 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.

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

4.92 out of 5 average rating, 102 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.

Top guest favorite

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

4.99 out of 5 average rating, 144 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.

Top guest favorite

A cozy entrance is seen under a covered porch, featuring two small chairs and a welcoming door. The area is surrounded by green grass and trees, with a gravel driveway leading up to the entrance. A picnic table is positioned on the lawn nearby.

Guesthouse in Durham

4.99 out of 5 average rating, 189 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.

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

4.97 out of 5 average rating, 297 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.

Superhost

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

4.72 out of 5 average rating, 234 reviews

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