
Holiday rentals in Cape Ann
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Top-rated holiday rentals in Cape Ann
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Other great holiday rentals in Cape Ann
Guest favourite

Home in Gloucester
4.96 out of 5 average rating, 28 reviewsBeach House on a Private Beach!
ToriRating, 5 stars1 week ago
Oh my goodness. This place was a DREAM. Such a beautiful home with a view you can’t top. My husband and I stayed with our children and two friends for an east coast summer getaway and we could not have found a better place. Awesome setup, view, and Gaby could not have been more helpful. We would love to stay here again.
Superhost

Cottage in Rockport
4.72 out of 5 average rating, 87 reviewsQuaint Oceanfront Cottage in Rockport MA
CindyRating, 5 stars9 months ago
Great little place for two! Sandy the neighbor was great along with her dog! 😊 great walking distance to shopping and restaurants! View is beautiful and breathtaking 😎will be back again in two years! Cindy and Gary from Ontario
Guest favourite

Flat in Rockport
4.97 out of 5 average rating, 34 reviewsArtistic studio with garden, walk to town/beaches
GlauciaRating, 5 stars6 days ago
This place is amazing! The outside is beautiful and the inside! I spent the weekend there with my daughter, and we walked everywhere! The small shops and restaurants were amazing. The host also provided lots of board games so we would play games when we got back. The studio is super cozy and lovely. I will book it again the next time we go back to Rockport!
Top guest favourite

Home in Rockport
5 out of 5 average rating, 10 reviewsWhale Cove Waterview
SusanRating, 5 stars7 months ago
Beautiful place just a one minute ride to the Rockport Golf Club where my daughter was getting married. We had plenty of room for all six of us. A nice big kitchen with a very large center island so we could share many meals and prepare food and platters for the wedding. The living room has a lovely gas fireplace and we had many cozy evenings there as we destressed from all the wedding festivities. We spent quite a lot of time outdoors, walking down to the ocean and sitting on the deck, watching the stars. October is a lovely time to visit Rockport. Less traffic, pretty autumn colors, no big crowds at restaurants so short wait for tables. If we needed to come back for another event, I would choose this home again. *for those with back issues- all of the beds were cozy but not supportive and very soft.
Top guest favourite

Guest house in Rockport
5 out of 5 average rating, 242 reviewsSea Mist Cottage Rockport, MA
DaveRating, 5 stars1 week ago
We’ve had the pleasure of renting John & Linda’s beautiful oceanfront cottage multiple times now—first for our engagement, then for the week after our wedding, and now for our anniversary and pregnancy announcement. This special place has become the backdrop for some of the most meaningful milestones in our lives. John & Linda are truly wonderful hosts—always providing excellent communication, thoughtful attention to detail, and a warm, welcoming atmosphere that makes the cottage feel like a home away from home. We’re so grateful for the memories we’ve made here, and we will absolutely be back!
Top guest favourite

Cottage in Rockport
5 out of 5 average rating, 10 reviewsBearskin Neck Old Garden Beach
DeborahRating, 5 stars6 days ago
I am originally from this area, we love the neighborhood we like to begin our day with walks, and you found lots of other people doing the same thing beautiful scenery. Out on one of our walks, we met the previous owner. He was so friendly polite, and I must use a phrase to describe the cottage from him. He said it’s everything you need and nothing you don’t! I smiled. He was exactly right. there are wonderful restaurants and beautiful antique shops to visit. There is a small beach access only two blocks away. There’s a place to sit up above where you can just enjoy the view. It’s quite the beautiful area. We had a wonderful time and the host was responsive, friendly and answered any of our questions so we thank you for that. Best, Michael & Deborah Carkonen
Top guest favourite

Apartment in Rockport
5 out of 5 average rating, 55 reviewsPanoramic Ocean Views in Rockport
ArianaRating, 5 stars2 days ago
Our stay at Jamila Casetta was absolutely wonderful! The location couldn’t be better—just a few minutes’ walk to all the shops and restaurants. The space was beautifully decorated, the bedding was super comfortable, and the kitchen had everything we needed. Communication with Christine was always smooth and helpful. We highly recommend this place and will definitely be back!
Superhost

Flat in Rockport
4.87 out of 5 average rating, 23 reviewsThe Orca – Modern Coastal Comfort Awaits
ThomasRating, 5 stars3 weeks ago
We had the pleasure of staying at The Orca for over a month while we were closing on a home in the area, and it truly became our cozy home away from home. The apartment is absolutely charming, with a perfect mix of historic character and modern comforts. The exposed beams and maritime accents give it such a warm, coastal feel, and the private patio with views of Bearskin Neck was a lovely spot to unwind after a busy day. The location couldn’t be more ideal—steps away from shops, restaurants, and the beach. We loved being in the heart of Bearskin Neck, with everything so easily accessible. The apartment was well-equipped with a full kitchen, comfy living space, Smart TV, and all the amenities we needed for a long stay. It really felt like a boutique retreat with thoughtful touches everywhere. A huge thank you to Matt for his flexibility and kindness throughout our stay. He was incredibly accommodating and made sure we had everything we needed. We truly appreciate the hospitality!
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- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Boston Common
- Revere Beach
- Fenway Park
- TD Garden
- Harvard University
- Lynn Beach
- Duxbury Beach
- York Harbor Beach
- North Hampton Beach
- New England Aquarium
- Long Beach
- Faneuil Hall Marketplace
- Freedom Trail
- Crane Beach
- Canobie Lake Park
- Prudential Center
- Long Sands Beach
- MIT Museum
- Good Harbor Beach
- Rye North Beach
- Museum of Fine Arts, Boston