Holiday rentals near Cape Ann

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September 2025

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Find the perfect private holiday rental within close proximity to Cape Ann. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as parking and a pool. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Cape Ann

Showing deals for:2 Jan - 9 Jan

Exceptional

(37 reviews)

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Gloucester, MA

8% off

for 7 nights, 1 home

AU$938 per night

includes taxes & fees

Gardenstone is your quaint and private getaway surrounded by nature.

Exceptional

(12 reviews)

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

Rockport, MA

8% off

for 7 nights, 1 home

AU$474 per night

includes taxes & fees

Your waterfront adventure awaits! Dive into endless fun and relaxation with stunning views right at your doorstep!

Exceptional

(5 reviews)

Oceanfront Dock Escape ~ Kayaks & Paddleboards

Gloucester, MA

11% off

for 7 nights, 1 home

AU$1,016 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

for 7 nights, 1 apartment

AU$488 per night

includes taxes & fees

Wonderful

(10 reviews)

Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed

Manchester-by-the-Sea, MA

8% off

for 7 nights, 1 home

AU$748 per night

includes taxes & fees

This bedroom features another King Size bed and convenient remote workspace

Exceptional

(26 reviews)

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

Rockport, MA

8% off

for 7 nights, 1 apartment

AU$497 per night

includes taxes & fees

A fully equipped kitchen with all new stainless appliances

Exceptional

(38 reviews)

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

Gloucester, MA

8% off

for 7 nights, 1 home

AU$505 per night

includes taxes & fees

Exceptional

(29 reviews)

Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

Gloucester, MA

8% off

for 7 nights, 1 home

AU$376 per night

includes taxes & fees

Exceptional

(15 reviews)

Charming Coastal Cottage, Steps to Ocean & Rockport Village!

Rockport, MA

8% off

for 7 nights, 1 cottage

AU$585 per night

includes taxes & fees

Exceptional

(32 reviews)

Large, open floor plan. Water views of Lanes Cove. Walk to Plum Cove beach.

Gloucester, MA

7% off

for 7 nights, 1 home

AU$349 per night

includes taxes & fees

Exceptional

(8 reviews)

Rarely Available Ocean Facing Walkable to Good Harbor Beach

Gloucester, MA

7% off

for 7 nights, 1 apartment

AU$570 per night

includes taxes & fees

Exceptional

(28 reviews)

Walk to the ocean, very private. Secluded, woodsy location.

Rockport, MA

8% off

for 7 nights, 1 apartment

AU$204 per night

includes taxes & fees

Exceptional

(54 reviews)

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

Rockport, MA

8% off

for 7 nights, 1 apartment

AU$669 per night

includes taxes & fees

Living Room Lounging Deck overlooking Motif #1

Exceptional

(98 reviews)

Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck

Rockport, MA

8% off

for 7 nights, 1 apartment

AU$589 per night

includes taxes & fees

Exceptional

(59 reviews)

Charming Studio, Private Bath, Kitchenette, Deck, Walk to Beach

Gloucester, MA

8% off

for 7 nights, 1 apartment

AU$247 per night

includes taxes & fees

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

Exceptional

(31 reviews)

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

Rockport, MA

8% off

for 7 nights, 1 home

AU$801 per night

includes taxes & fees

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Cape Ann

Find the best place to stay - Cape Ann

Premier Host

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Sleeps 8 · 4 bedrooms · 2 bathrooms

Premier Host

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Sleeps 18 · 10 bedrooms · 3+ bathrooms

Fantastic ocean views and 2 beaches! Read "About this property" for discounts

Sleeps 10 · 5 bedrooms · 2+ bathrooms

Top rated rentals - Cape Ann

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

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
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Holiday rentals near Cape Ann

Holiday rentals with weekly discounts - Cape Ann

Image gallery for Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Find spaces that suit your style

Find properties near top attractions in Cape Ann

Map Attractions

Cape Ann

Find the best place to stay - Cape Ann

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Top rated rentals - Cape Ann

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

Peace of mind

More quality time

All the privacy of home

More for less

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