Guesthouse vacation rentals in North Shore

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in North Shore

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

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Guest favorite

Guesthouse in Boston

4.99 out of 5 average rating, 233 reviews

The Red Door Carriage House

The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.

Mar 22 – 29

G$60,602 GYD per night

Guest favorite

Guesthouse in Durham

4.99 out of 5 average rating, 123 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/bath/laundry. 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 the Inn for drinks. Two smart tv's are available, wi-fi, and a small desk area. This efficient space is for 1-2 people. A small scale pull-out couch can sleep the 2nd, average-size person if desired.

Nov 6 – 13

G$31,713 GYD per night

Guest favorite

Guesthouse in Beverly

4.98 out of 5 average rating, 113 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.

Jan 4 – 11

G$37,710 GYD per night

Superhost

Guesthouse in Manchester

4.87 out of 5 average rating, 223 reviews

Spruce Studio (5 Minutes from Downtown & Elm St.)

Centrally located to many destinations, we hope this studio provides a cozy retreat from the hustle of the day; be it work, travel, adventuring, or taking in the sites of Manchester. With a full, bathroom, kitchenette, and a queen-size bed this space offers lots for the solo traveler, couple, or small family. We provide a smart TV for relaxing and a desk for more serious matters. We hope your stay in Manchester exceeds your imagination and that Spruce Studio surpasses all expectations.

Jul 19 – 26

G$19,260 GYD per night

Guest favorite

Guesthouse in North Andover

4.97 out of 5 average rating, 188 reviews

Spacious Studio Guesthouse at Winery w/ Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

Aug 16 – 23

G$90,429 GYD per night

Guest favorite

Guesthouse in Cohasset

4.98 out of 5 average rating, 106 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.

May 9 – 16

G$41,107 GYD per night

Guest favorite

Guesthouse in Gloucester

4.94 out of 5 average rating, 143 reviews

Jestina's Cottage - Next to Rocky Neck

Jestina's Cottage is walking distance to the Rocky Neck Art Colony, Gloucester Stage, restaurants, Niles Beach and a short bike ride to Good Harbor Beach. You’ll love the cottage because of the ambience and the location; you feel like you are lost in the woods of Maine but you are close to everything. The cottage is great for couples, solo adventurers, business travelers, and pet-friendly.

Sep 29 – Oct 6

G$33,218 GYD per night

Guest favorite

Guesthouse in Framingham

4.98 out of 5 average rating, 203 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.

Nov 22 – 29

G$23,207 GYD per night

Guest favorite

Guesthouse in Marblehead

4.91 out of 5 average rating, 198 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.

Sep 2 – 9

G$41,679 GYD per night

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 171 reviews

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. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.

Jul 30 – Aug 6

G$30,730 GYD per night

Guest favorite

Guesthouse in Kittery

5.0 out of 5 average rating, 274 reviews

Kittery Cottage - Newly built 2020

Kittery Cottage is a private, newly built property located 1.5 miles from the charming city of Portsmouth and minutes from many of the seacoast beaches. With a ten minute walk to Kittery Foreside you have access to many restaurants and shops. The Kittery outlets are less than 2 miles away.

Mar 3 – 10

G$69,533 GYD per night

Guest favorite

Guesthouse in Scituate

4.97 out of 5 average rating, 209 reviews

Scituate “Pura Vida" Suite

Brand new cozy apartment just one block from Scituate Harbor. Beautiful floors, bright space & lighting. Walking distance to all coffee shops, restaurants, bars, stores, supermarket, main beaches. Check out our vacation villa in Costa Rica https://www.airbnb.com/h/villaocaso

Nov 16 – 23

G$39,824 GYD per night