Holiday rentals near Cape Ann
We found 434 holiday rentals — enter your dates for availability
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:14 Nov - 21 Nov
Image gallery for Coastal Cottage on Private Island, overlooking the Essex Great Marsh
1010 out of 10 rating
Exceptional
(10 reviews)
Coastal Cottage on Private Island, overlooking the Essex Great Marsh
Essex, MA
12% off
Price is NZ$6,031
NZ$6,031
NZ$862 per night
includes taxes & fees
Image gallery for Long Beach Suites: Book 2025 Summer Trip Today!
8.68.6 out of 10 rating
Excellent
(10 reviews)
Long Beach Suites: Book 2025 Summer Trip Today!
Gloucester, MA
7% off
Price is NZ$2,651
NZ$2,651
NZ$379 per night
includes taxes & fees
Image gallery for Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
Rockport, MA
7% off
Price is NZ$3,035
NZ$3,035
NZ$434 per night
includes taxes & fees
Image gallery for Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
Gloucester, MA
8% off
Price is NZ$7,189
NZ$7,189
NZ$1,027 per night
includes taxes & fees
Image gallery for Stunning Views from Beachfront House in Manchester-by-the-Sea!
1010 out of 10 rating
Exceptional
(68 reviews)
Stunning Views from Beachfront House in Manchester-by-the-Sea!
Gloucester, MA
8% off
Price is NZ$12,436
NZ$12,436
NZ$1,777 per night
includes taxes & fees
Image gallery for 2 Bd/2 Bth with ·King bed ·2 floors · Private Parking · Downtown Rockport
9.89.8 out of 10 rating
Exceptional
(8 reviews)
2 Bd/2 Bth with ·King bed ·2 floors · Private Parking · Downtown Rockport
Rockport, MA
8% off
Price is NZ$3,246
NZ$3,246
NZ$464 per night
includes taxes & fees
Image gallery for Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed
Manchester-by-the-Sea, MA
8% off
Price is NZ$4,686
NZ$4,686
NZ$669 per night
includes taxes & fees
Image gallery for Quaint & Cozy Rockport Gem ~ Walk to Sea ~ BBQ & Private Parking!
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Quaint & Cozy Rockport Gem ~ Walk to Sea ~ BBQ & Private Parking!
Rockport, MA
8% off
Price is NZ$4,206
NZ$4,206
NZ$601 per night
includes taxes & fees
Image gallery for Walk to Good Harbor and Long Beach -Vacation Home
8.88.8 out of 10 rating
Excellent
(8 reviews)
Walk to Good Harbor and Long Beach -Vacation Home
Gloucester, MA
8% off
Price is NZ$5,159
NZ$5,159
NZ$737 per night
includes taxes & fees
Image gallery for The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·
9.89.8 out of 10 rating
Exceptional
(20 reviews)
The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·
Rockport, MA
8% off
Price is NZ$3,175
NZ$3,175
NZ$454 per night
includes taxes & fees
Image gallery for Rockport direct Waterfront 3 bedroom, 3 bathroom home
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Rockport direct Waterfront 3 bedroom, 3 bathroom home
Rockport, MA
8% off
Price is NZ$8,384
NZ$8,384
NZ$1,198 per night
includes taxes & fees
Image gallery for C by the Sea - Ocean View Penthouse
1010 out of 10 rating
Exceptional
(8 reviews)
C by the Sea - Ocean View Penthouse
Gloucester, MA
8% off
Price is NZ$6,042
NZ$6,042
NZ$863 per night
includes taxes & fees
Image gallery for ❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything
9.69.6 out of 10 rating
Exceptional
(26 reviews)
❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything
Essex, MA
21% off
Price is NZ$5,886
NZ$5,886
NZ$841 per night
includes taxes & fees
Image gallery for #Weddings #Holidays #Corporate short term? Just need some “in between” place ?
1010 out of 10 rating
Exceptional
(5 reviews)
#Weddings #Holidays #Corporate short term? Just need some “in between” place ?
Gloucester, MA
8% off
Price is NZ$3,922
NZ$3,922
NZ$560 per night
includes taxes & fees
Image gallery for 3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
1010 out of 10 rating
Exceptional
(33 reviews)
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
Gloucester, MA
7% off
Price is NZ$3,201
NZ$3,201
NZ$457 per night
includes taxes & fees
Image gallery for Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA
Gloucester, MA
7% off
Price is NZ$2,902
NZ$2,902
NZ$415 per night
includes taxes & fees
Image gallery for Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!
1010 out of 10 rating
Exceptional
(30 reviews)
Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!
Gloucester, MA
8% off
Price is NZ$6,237
NZ$6,237
NZ$891 per night
includes taxes & fees
Image gallery for Charming Coastal Cottage, Steps to Ocean & Rockport Village!
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Charming Coastal Cottage, Steps to Ocean & Rockport Village!
Rockport, MA
8% off
Price is NZ$5,159
NZ$5,159
NZ$737 per night
includes taxes & fees
Image gallery for Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
9.89.8 out of 10 rating
Exceptional
(117 reviews)
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
Gloucester, MA
8% off
Price is NZ$4,420
NZ$4,420
NZ$631 per night
includes taxes & fees
Image gallery for VIEWS! Annisquam Bridge House at Lobster Cove. June dates discounted.
9.89.8 out of 10 rating
Exceptional
(27 reviews)
VIEWS! Annisquam Bridge House at Lobster Cove. June dates discounted.
Gloucester, MA
8% off
Price is NZ$2,841
NZ$2,841
NZ$406 per night
includes taxes & fees
Image gallery for Beach & King - Stunning Ocean Views!
1010 out of 10 rating
Exceptional
(51 reviews)
Beach & King - Stunning Ocean Views!
Rockport, MA
8% off
Price is NZ$17,151
NZ$17,151
NZ$2,450 per night
includes taxes & fees
Image gallery for NEW Rockport Studio · Walk to Bearskin Neck · Reserved Parking
1010 out of 10 rating
Exceptional
(17 reviews)
NEW Rockport Studio · Walk to Bearskin Neck · Reserved Parking
Rockport, MA
8% off
Price is NZ$2,349
NZ$2,349
NZ$336 per night
includes taxes & fees
Image gallery for You will love our location and will return for our hospitality!
9.69.6 out of 10 rating
Exceptional
(52 reviews)
You will love our location and will return for our hospitality!
Rockport, MA
16% off
Price is NZ$2,923
NZ$2,923
NZ$418 per night
includes taxes & fees
Image gallery for Walk to Good Harbor Beach. 3BR home, NEW Kitchen
1010 out of 10 rating
Exceptional
(98 reviews)
Walk to Good Harbor Beach. 3BR home, NEW Kitchen
Gloucester, MA
8% off
Price is NZ$4,600
NZ$4,600
NZ$657 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Cape Ann
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Find the best place to stay - Cape Ann
Refreshing Ocean and Sunset View
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
189 reviews(189 reviews)
Coastal Comfort—Walk to Beach & Cafés
Sleeps 6 · 3 bedrooms · 2 bathrooms
A Beautiful "WEE " Place By The Sea in Rockport
Sleeps 5 · 2 bedrooms · 1 bathroom
8.48.4 out of 10
Very goodvery good
38 reviews(38 reviews)
Beautiful Newly Built Custom Home, Spectacular Ocean Views
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value