
Guest house holiday rentals in North Shore
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Top-rated guest house rentals in North Shore
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Family-friendly guest house rentals

Private room w/ private bath - single family house
Wonderful location, quiet residential neighborhood but close to Porter Square for the bus, subway, and train. Jane and Alan are such gracious hosts as well!

Private Guest House
Delia was amazing! We needed a place to stay with 3 dogs while our house in NH sold and We could close on new house. She was so good to us! Has a beautiful property, We enjoyed the fenced in yard & hot tub

Spacious 3 bedroom Suite Sleeps 6-8. 4 Beds
Wendy and Doug’s upstairs suite of rooms is roomy, very comfortable, quiet and super convenient to downtown Salem without being right in the middle of the crowds. We walked to downtown easily. Wendy was so helpful especially when we had a last mins dress alterations project, offering up her sewing machine so the work was done in time for the evening’s event. Overall a lovely stay.

Cute Beach Cottage
It was a cozy beach cottage, and more. Perfect for two couples, clean with comfortable beds. Great location to walk to local attractions, even in the rain!

Lake Front, Beautiful, Private Studio w/Kayaks
Fran was a wonderful hostess! She was very flexible and accommodating as our original plans changed and we ended up bringing our kids with us as well. She greeted us when we arrived later at night and graciously allowed us to stay in a larger cottage to accommodate my kids which we are forever grateful for! 🤍 the views are breathtaking - what a serene and peaceful spot! We enjoyed every minute we spent in the cottage as well as exploring the town. We would stay here anytime!

Country Cottage in the City
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.

Airy new apt for 2-6. Near subway. Free parking.
Woody and Pauline are fantastic hosts and their beautiful apartment was the perfect home-base for our recent trip to Boston. The T is really only a block and a half away and you can access all of Boston from the T. Jamaica Plain is adorable and there’s lots of beautiful green spaces nearby. JPizle was fantastic and Evergreen Coffee was also good. Both within easy walking distance. Everyone is super friendly. If you are not familiar with the streets, it can be really hard to navigate getting to the house from the interstate or back again. A tiny neighborhood Whole Foods is a 6 minute drive away. The bedroom downstairs was a little stuffy for us, but we just moved the fan from upstairs down and Pauline said it was okay. Otherwise we were very comfortable and really enjoyed our stay. The antique furniture was lovely, the space was spotless, and the location was perfect!
Guest house rentals with a patio

Charming Guesthouse with Access to Private Beach
Absolutely beautiful spot and hosts were wonderful. Access to the local beach was an awesome bonus to this adorable spot.

Modern & Cozy Apartment
Edna was very friendly and quick to respond to messages throughout my stay. The space was quiet and cozy. I enjoyed my stay and would definitely stay here again when I return.

Sunny Airy Modern Oceanfront Cottage w/ Deck Wi-Fi
Very responsive extremely nice

Adorable 1 bedroom guest house with ocean view
We enjoyed our 2 day stay at Brad’s cottage. Home was easily accessible and the location was fantastic. We watched the sunrise from the bedroom and enjoyed late afternoon walks on the beach. As our son may be relocating to this area of Mass, we spent the days exploring the area. The cottage was comfortable and clean. Brad was readily accessible and responsive. We would definitely return .

The Groveside Guest House
I needed a place to stay for a funeral and was t wanting to be stuck in a hotel so I tried out Catherine’s guest house. It’s a great little house, probably around 800 sqft total on the back side of the main house. Everything was exactly like the picture. Walking distance to a lot of things, including downtown Concord. Catherine was wonderfully responsive and helped me with a few logistical questions I had as well. Would suggest to anyone needing a simple place to stay. Couldn’t really do more than two folks at best who are good sharing a bed. The stairs are steep as well so bear that in mind if it’s an issue as the restroom is upstairs. Great for relaxing and enjoying a trip. Has a nice bird feeder that is visible from the living room area as well. Had birds the entire time, rain or shine.

Heron's Nest on North Mill Pond
The Heron’s Nest was an awesome place to stay in Portsmouth. It is close to downtown which has lots of great restaurants. The bed was very comfortable and the backyard was so much fun to sit and watch so many different kinds of birds. Walter and Mary Ellen are some of the nicest hosts we have stayed with. I highly recommend staying at the Heron’s Nest!

The Genkan • Scituate's Cozy Harbor Guesthouse
Very peaceful stay in this cool space! Would highly recommend. Really great location for exploring Scituate.

Luxurious Executive Suite
A quiet place to stay for a few days. It's a drive to most places but that was not a problem for us. Tracey was responsive and the stay was as advertised.
Guest house rentals with a washing machine and dryer

Luxury Guest House on quiet 4 Acre property
We have had a wonderful experience at this Airbnb. The accommodations are excellent and George is an excellent host. We would highly recommend this to anyone visiting the Dover area. Our dog has been welcomed and appreciated. Bill & Cathy

Private Studio Guest House w/ Free Parking
Cosy and convenient stay with all the amenities we could ask for. A few minutes walk to the red line, giving quick transport connections throughout the city.

Cute mill house: 3BR•Wood stove *Brkfst included*
We came to Natalie’s place for a baby shower in a neighboring town and are so lucky we found such a homey place! The house is very kid friendly with lots of musical instruments and books around which helped our little one feel at home in a new place. The breakfast treats were tasty and thoughtful. The wood stove was the perfect cozy feature to end each night! Highly recommend!!

Enchanted Cottage on 5 Acres
We have stayed here before and it’s always been wonderful! Truly is an enchanted cottage where you can watch the bunnies in the garden and be secluded from the hustle and bustle of Framingham even tho it’s right in town! Decorated comfortably with antiques and kitchen well stocked! Walkable or easy drive to amenities downtown. Close enough to travel to Brimfield Antique Markets. Barry is so friendly and will do whatever is needed for his guests to be happy and communicates readily! We love it!

Spacious Suite 15 mi from Boston
Mia’s place looks better than the pictures, very clean, communication was nice and smooth. Check out time is 10am instead of the 11am the app stills shows but she communicates everything in a time matter

Modern, Cute 2 BR Carriage House North of Boston
This place is a gem. Walkable to the Orange Line or a two minute drive with very affordable parking at the T station. It would have been an easy drive but with the T so close….why not use it?! The house is clean, spacious and was great for our family of 4. Melrose itself offers a lot so there’s just so many nice options close by. Will stay here again.

HARBOR VIEW SUITE
Lori’s place was wonderful. It is within walking distance to local shops and restaurants and has great views of the harbor. It is so calming and pleasant to sit and watch boats coming and going and knowing the local fish market has the freshest catch each day. She thought of everything you would need and it is also very tastefully decorated. We loved this place and will definitely return. Highly recommend !

Lovely 1 Bedroom Guest House. Downtown Cohasset
Everything about my experience was perfect! Joanne goes above and beyond to make you feel comfortable and her place is absolutely beautiful It was immaculate and the decorating was adorable even a nice touch of flowers on the table. If I ever go back to the area I would most certainly contact Joanne again to stay there If anyone is considering a place look no further contact Joanne Thank you Joanne for a perfect Experience
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- Hampton Beach
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