Cape Anne Holiday Rentals

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Holiday Rentals in Cape Anne

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Chesapeake Bayside Loft

8.0 out of 10, Very good, (12)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
Chesapeake Bayside Loft

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
8.0 out of 10, Very good, (4)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (176)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (48)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"We had a great time! The house was really nice, very comfortable and clean. It had everything that you needed. I really liked that everything was controlled by alexa even the window blinds. I definitely recommend staying here and I definitely will be returning. "
The Cozy Crab- Your Charming Haven in Lovely North Beach!

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (75)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is NZ$781
includes taxes & fees
22 July - 23 July
Waterfront Oasis of Annapolis Star

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is NZ$462
includes taxes & fees
23 July - 24 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (33)
"Such a cute and unique place to stay. Very peaceful. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (11)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (42)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 4 Bedroom Home w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"A group of us stayed here for a friends wedding and had a wonderful time! The hosts were communicative and friendly. The house is amazing! Comfortable, big, well laid out. The hot tub was perfect temp and clean. The beds were comfortable. Having a yard was great for our dog. Would definitely stay here again and highly recommend this place!"
The price is NZ$921
includes taxes & fees
23 July - 24 July
Spacious 4 Bedroom Home w/ Hot Tub

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

9.6 out of 10, Exceptional, (24)
"Was the perfect spot for a nice weekend getaway with some friends."
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is NZ$569
includes taxes & fees
24 July - 25 July
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (79)
"Excellent stay. We look forward to returning."
Romantic Two Bedroom Condo

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (74)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (64)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes
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

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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Cape Anne is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Cape Anne?

Expedia has 3 holiday rentals for your stay in Cape Anne.

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

While exploring the area, visit family-friendly sights like Chesapeake Beach Water Park, or get outside and enjoy nature at Shadyside Park. Triton Beach and Chesapeake Beach Railway Museum 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.