Cape Anne Holiday Rentals

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Holiday Rentals in Cape Anne

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
10.0 out of 10, Exceptional, (14)
"Everything was exactly as described on the listing. It’s the perfect spot for a peaceful and relaxing getaway, all while being close to a charming town. The hosts were very pleasant and easy to communicate with. I highly recommend this place! "
United States
Michael T.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (12)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
United States
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (42)
"Everything you need without the crowds of full size hotels"
United States
Sharon M.
Cass-N-Reel Luxury Houseboat
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
United States
Lynne J.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (122)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"First, Brett is an exceptional host. Very helpful and responsive. This is a very special place in a wonderful community with incredible views. Rustic, warm and the perfect place to relax. We didn’t want to leave! Highly recommend."
United States
Dee D.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is NZ$536
includes taxes & fees
29 Oct - 30 Oct
Waterfront Getaway, Dock Your Boat & Play!
Luxury Waterfront Executive Family Home Annapolis with All Amenities
7.2 out of 10, Good, (5)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
United States
Kristin W.
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (144)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (237)
"This was a wonderful historic home to vacation in"
United States
Amy N.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
9.4 out of 10, Exceptional, (16)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
United States
Kerry G.
The price is NZ$2,011
includes taxes & fees
9 Nov - 10 Nov
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (37)
"Fabulous place. We’ll be booking again next year. "
United States
Steve R.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (31)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is NZ$529
includes taxes & fees
2 Nov - 3 Nov
Large 2 bedroom house with private parking in a nice neighborhood
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"Wonderful home and host. Very easy to check-in and communication was excellent. "
United States
Ann T.
The price is NZ$534
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (23)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is NZ$1,006
includes taxes & fees
29 Oct - 30 Oct
Edgewater/Mayo Gateaway w/ Hot Tub
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (129)
"We just enjoyed our fourth year at Million Dollar View of the Chesapeake Bay and already look forward to our next vacation at this wonderful home!"
United States
Melissa G.
Million Dollar View of the Chesapeake Bay
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
9.8 out of 10, Exceptional, (43)
"House was beautiful! Right on the bay and easily accommodated our group. "
United States
James T.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (221)
"Very nice place, we will be visiting again!"
United States
Karen B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
United States
David W.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cape Anne Hotel Reviews

Find out more about Cape Anne

Everything you need to know about Cape Anne holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cape Anne holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cape Anne holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cape Anne holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cape Anne. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cape Anne holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cape Anne holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cape Anne rentals

At Expedia, we put the best Cape Anne holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cape Anne rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cape Anne holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cape Anne. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Cape Anne?

Yes, there are holiday rentals close to the most popular sights in Cape Anne, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cape Anne has to offer?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of Cape Anne is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Cape Anne?

Expedia has 4 holiday rentals for your stay in Cape Anne.

What’s there to see and do in Cape Anne?

Chesapeake Bay and Northern Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Shadyside Park and Smithsonian Environmental Research Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Cape Anne like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cape Anne. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family gatherings.