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Top Holiday Rentals in Cape Anne

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

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

10.0 out of 10, Exceptional, (177)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (31)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
6.8 out of 10, (5)
"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "
Floating 2 bed 2 bath condo stunning views of the bay

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 £378
includes taxes & fees
19 Aug - 20 Aug
Waterfront Oasis of Annapolis Star

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.

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is £290
includes taxes & fees
11 Aug - 12 Aug
Waterfront Getaway, Dock Your Boat & Play!

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (35)
"Such a cute and unique place to stay. Very peaceful. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

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

10.0 out of 10, Exceptional, (228)
"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!

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

9.8 out of 10, Exceptional, (44)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

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 £258
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (81)
"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, (76)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
Bay views with kayaks, bikes, fire pit, crabbing and more

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

10.0 out of 10, Exceptional, (50)
"Beautiful home with LOTS of attention to detail. The backyard was a beautiful oasis and we LOVED the “swing bed” on the screened-in porch. Mark and Karen add lots of fine touches to make your stay special. Plenty of room for two, cozy for four, and comfortable for four legged friends with the fenced in back yard. Quiet and private with a short 10 minute drive to town. Can’t wait to return!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (24)
"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (121)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (39)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (11)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is £1,020
includes taxes & fees
12 Aug - 13 Aug
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Cape Anne offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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?

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 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.