Holiday rentals near Dogtown

We found 1,013 holiday rentals — enter your dates for availability

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July 2025

August 2025

Take a look at private holiday rentals within easy reach of Dogtown that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, including Wi-Fi and parking. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Dogtown

Showing deals for:17 Oct - 24 Oct

Exceptional

(7 reviews)

NEW 2BR Historic Marblehead Home+Minutes to Beach

Marblehead, MA

8% off

AU$1,338 per night

includes taxes & fees

Exceptional

(18 reviews)

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Rockport, MA

8% off

AU$606 per night

includes taxes & fees

Exceptional

(16 reviews)

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Gloucester, MA

8% off

AU$599 per night

includes taxes & fees

Gardenstone is your quaint and private getaway surrounded by nature.

Exceptional

(10 reviews)

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Rockport, MA

8% off

AU$599 per night

includes taxes & fees

Welcome to Plum Island Cottage! A private house with a backyard and deck.

Exceptional

(70 reviews)

Former Carriage House on Plum Island Massachusetts

Newburyport, MA

8% off

AU$628 per night

includes taxes & fees

Cozy and uniquely designed living room space on the lower level

Exceptional

(8 reviews)

2 Bd/2 Bth with ·King bed ·2 floors · Private Parking · Downtown Rockport

Rockport, MA

8% off

AU$586 per night

includes taxes & fees

This bedroom features another King Size bed and convenient remote workspace

Exceptional

(20 reviews)

The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·

Rockport, MA

8% off

AU$582 per night

includes taxes & fees

Exceptional

(7 reviews)

2BR/2BA Harborside Home · Fenced Backyard · Ocean View ·Walk to Rocky Neck+Beach

Gloucester, MA

8% off

AU$760 per night

includes taxes & fees

Exceptional

(27 reviews)

Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

Gloucester, MA

8% off

AU$813 per night

includes taxes & fees

Exceptional

(57 reviews)

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Marblehead, MA

8% off

AU$815 per night

includes taxes & fees

Exceptional

(117 reviews)

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

Gloucester, MA

8% off

AU$639 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Dogtown

Artistic guest suite with beautiful outdoor spaces, walk to town & beaches

Sleeps 2 · 1 bathroom

Top rated rentals - Dogtown

Premier Host

Highly-Recommended Getaway in Marblehead

Conveniently located and well maintained, this cottage was the perfect lodging for my solo vacation to the region. The well-stocked kitchen, spacious bathroom, and wood-burning stove (very easy to start) were just some of its many amenities. The one-page list of house rules and instructions was clear and easy to follow, which I greatly appreciated. And it was apparent that the property had been thoroughly cleaned and prepared for my arrival. Overall, I couldn’t have been more pleased with my stay, and I will certainly keep this gem in mind for future trips. Thank you, property owners!

Heather M.

Stayed Mar 2021

Peace of mind
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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value