Cape Ann Luxury Holiday Homes
List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 km
253 rentals in Cape Ann.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Directly on Long Beach Rockport MA
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Artist's Studio turned Guest House Sleeps up to 3
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Good Harbor Beach House
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
4 Bedroom LUX House/with Pool Next Door
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Quality Accommodations in Quiet Seaside Village
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Beautiful Oceanfront Home in Estate Setting in Gloucester
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Newly Renovated!! Beautiful 3 bed home...steps from beach!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Sunset Views, Waterfront Property, Dock - Sleeps 12
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Save time - get the best Cape Ann rentals sent straight to your email!
'We can't wait to return to Four Winds'
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Jul 12-16 OPEN! SUNSET STUDIO w/Scenic Harbor View
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Featured on HGTV's Beach Hunters
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
'Absolutely lovely. The cottage, the beach, the town, the owners.'
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Fantastic ocean views and only steps to Long and Cape Hedge Beaches
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Good Harbor Beach House - Walk to Shops
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester)
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
4 Bedroom Cottage With Singing Beach Access
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Prime Gloucester Property - Overlooking Harbor w Pool
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Perfect Good Harbor Beach vacation home for large and/or extended family getaway
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Amazing Twin Light Sea Views from Vintage Stonewalled Cottage at Rocky Shores!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Come home to Rockport!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
2 Bedroom Waterfront Unit, Vacation or Short Term Rental
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Holbrook House: Charming Rockport Village Cottage, Walk To Everything!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Luxury Home in the Heart of Rockport
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Old Garden Beach Short Walk to Beach & Town
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Perfect apartment for a single or couple.
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Gladview Rockport Apt #gladview#thacher
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Spectacular, luxury waterfront property directly overlooking Sandy Bay.
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Spacious, Comfortable Family Home with Gorgeous Gardens near Ocean and Downtown
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Long Beach-Gloucester-1 minute walk to Beach Lovely setting & big yard. Sleeps 6
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Cape Ann, Annisquam panoramic ocean views from every room.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Perfect Rockport Vacation Destination
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Waterfront Home with Spectacular Viewsof the Annisquam River
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Romantic SUMMERWIND COTTAGE- Scenic Harbor View
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Walk to Good Harbor Beach, pet friendly, family beach home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Waterfront House onThe Old Harbor Spectacular Views
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
SERENITY BY THE SEA - GLOUCESTER, MA
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
123456