North Shore Massachusetts Vacation Rentals

Compare 26 vacation rentals.
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Make North Shore Massachusetts your next getaway

Explore our vacation rentals in North Shore Massachusetts. Our private accommodations include everything you need to have the perfect getaway, whether you're here for a family vacation, couples retreat, or making memories with friends.

Top North Shore Massachusetts property types

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House rentals

View 21 House rentals
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Cottages

View 2 Cottages
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Studios

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Popular amenities for North Shore Massachusetts vacation rentals

Popular
Dog-friendly Hot tub Internet
Longview House
4 Bedroom | 2.5 Bath | Sleeps 9

Longview House - Gloucester, MA

$336 avg / night
(excludes fees and taxes)
4.5 (10)
Vintage Rockport Escape
3 Bedroom | 2 Bath | Sleeps 6

Vintage Rockport Escape - Rockport, MA

$232 avg / night
(excludes fees and taxes)
4.48 (128)
Great Ledges Studio
0 Bedroom | 1 Bath | Sleeps 2

Great Ledges Studio - Rockport, MA

$147 avg / night
(excludes fees and taxes)
4.8 (10)
Paula's Suite
2 Bedroom | 2 Bath | Sleeps 4

Paula's Suite - Gloucester, MA

$278 avg / night
(excludes fees and taxes)
4.77 (31)
Point Radio Cottage
1 Bedroom | 1.5 Bath | Sleeps 4 (2 Adults Max)

Point Radio Cottage - Gloucester, MA

$331 avg / night
(excludes fees and taxes)
4.83 (58)

View 21 more homes

Recent North Shore Massachusetts guest reviews

We just did a short 2 night stay with the kids and our small dog, but we would love to return. The views are amazing and it feels so quiet and private, even though it’s only a few mins walk to parks and beaches. There’s so much to do, so close by. The landscaping and outdoor spaces are incredibly stunning. Very special place to stay while in Gloucester!
Vicky G. | May 2026
This was a gorgeous home full of character. We enjoyed our honeymoon here and the top floor room with the tub was amazing! The only things I would note are, having a TV in the top floor room would have been amazing and there was a stair on the top floor staircase that felt like it was going to cave in, so we avoided that step just as an FYI!
Madison W. | May 2026
Point Radio Cottage is one of those rare rentals that looks great online and is even better in person. The setting is stunning, the cottage is comfortable and well cared for, and it’s perfectly located for exploring Cape Ann. We enjoyed it so much we booked a return stay before finishing our first visit. Location & Views The cottage sits on the grounds of a beautiful coastal property with phenomenal water views. It’s just minutes from Gloucester (and walkable if you’re up for a longer stroll along a gorgeous coastline), with easy drives to Rockport and Manchester-by-the-Sea. Salem is also a doable day trip. The Cottage The cottage is well-appointed and extremely comfortable. The upstairs is a private primary suite (bedroom and bath), which made it feel spacious and quiet. Everything was thoughtfully set up for a relaxing stay. Character & History A fun bonus is the property’s history: the cottage was constructed above a foundation constructed for what John Hays Hammond originally intended to have been his Castle. The owners provide a comprehensive notebook explaining the background, and the well-stocked bookshelves include Hammond’s autobiography for anyone who wants to dive deeper. Outdoor Space & Pet Friendly This was a fantastic place to stay with our dogs—they settled in immediately. The landscaped grounds are great for wandering, and there’s a sidewalk along Western Avenue to Stage Fort Park for a longer walk. If you’re more adventurous, there are stone steps down to a rocky beach at the base of the cottage. Bottom line: If you’re looking for a peaceful Cape Ann getaway with incredible scenery, easy access to nearby towns, and a comfortable cottage with real character, Point Radio Cottage is an excellent choice. We can’t wait to return.
Doug T. | Apr 2026
North Shore Massachusetts vacation rental FAQ

Yes, 8 of our North Shore Massachusetts homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 26 of our North Shore Massachusetts vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our North Shore Massachusetts vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local North Shore Massachusetts team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for North Shore Massachusetts, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
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Professional cleaning