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Holiday rentals near Thatcher's Island

We found 390 holiday rentals — enter your dates for availability

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August 2025

September 2025

Select the perfect holiday rental that's near Thatcher's Island. Holiday homes offer the best amenities for your family, friends or furry companion, such as air conditioning and cable TV. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Thatcher's Island

Showing deals for:31 Oct - 7 Nov

Excellent

(10 reviews)

Long Beach Suites: Book 2025 Summer Trip Today!

Gloucester, Massachusetts

8% off

AU$466 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$483 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$493 per night

includes taxes & fees

Exceptional

(29 reviews)

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

Gloucester, MA

8% off

AU$822 per night

includes taxes & fees

Exceptional

(117 reviews)

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

Gloucester, MA

8% off

AU$579 per night

includes taxes & fees

Exceptional

(5 reviews)

#Weddings #Holidays #Corporate short term? Just need some “in between” place ?

Gloucester, MA

8% off

AU$513 per night

includes taxes & fees

The studio is a light and bright yet colorful open space

Exceptional

(16 reviews)

NEW Rockport Studio · Walk to Bearskin Neck · Reserved Parking

Rockport, MA

8% off

AU$380 per night

includes taxes & fees

Exceptional

(22 reviews)

Adorable Beach house with lots of outdoor space and steps to Long Beach!

Rockport, MA

7% off

AU$716 per night

includes taxes & fees

Exceptional

(49 reviews)

Harborfront House Directly on Rockport’s Quiet and Beautiful Old Harbor

Rockport, MA

8% off

AU$629 per night

includes taxes & fees

Living Room Lounging Deck overlooking Motif #1

Exceptional

(95 reviews)

Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck

Rockport, MA

8% off

AU$595 per night

includes taxes & fees

The Nest...all the comforts of home in a newly renovated 1900 farmhouse

Exceptional

(29 reviews)

The Nest at Pigeon Cove: Modern farmhouse with all the comforts of home!

Rockport, MA

8% off

AU$882 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find properties near top attractions in Thatcher's Island

Thatcher's Island

Find the best place to stay - Thatcher's Island

Showing deals for: 31 Oct - 3 Nov

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Sleeps 8 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$1,131 per night

includes taxes & fees

Walk to Good Harbor Beach, pet friendly, family beach home

Sleeps 8 · 3 bedrooms · 1+ bathroom

for 3 nights, 1 home

AU$765 per night

includes taxes & fees

Centrally located charmer with expansive patio, board games, & central AC

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

AU$534 per night

includes taxes & fees

Top rated rentals - Thatcher's Island

Premier Host

Exactly what we were hoping for on a one week vacation escape.

We wish to thank Diane for providing my wife and I with the lovely, quaint accommodations for one week. It was exactly what we were hoping to find when we arrived in mid Jun 2016. The one bedroom unit was very clean and included every feature you could wish for in a rental unit. The kitchen was well stocked, the bedroom very comfortable and the view from the second floor deck was perfect when my wife and I shared morning coffee. We just hope it's available on a future visit.

Sandy p.

Stayed June 2016

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