Cape Anne Holiday Rentals

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Holiday Rentals in Cape Anne

Sunset Cottage - West River Access and Views!

2.0 star property
Shady Side
Sunset Cottage - West River Access and Views!

Historic Downtown Luxury • USNA • Waterfront

Historic District
The price is AU$949
includes taxes & fees
11 Nov - 12 Nov
Historic Downtown Luxury • USNA • Waterfront

Upscale Condo in Annapolis

Historic District
10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
The price is AU$946
includes taxes & fees
9 Dec - 10 Dec
Upscale Condo in Annapolis

#2 Egret Cottage Harris Cove

Saint Michaels
10.0 out of 10, Exceptional, (1)
The price is AU$598
includes taxes & fees
23 Nov - 24 Nov
#2 Egret Cottage Harris Cove

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

Stevensville
9.6 out of 10, Exceptional, (31)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is AU$406
includes taxes & fees
12 Nov - 13 Nov
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
The price is AU$431
includes taxes & fees
21 Nov - 22 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is AU$483
includes taxes & fees
23 Nov - 24 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick
9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AU$606
includes taxes & fees
11 Nov - 12 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AU$551
includes taxes & fees
1 Dec - 2 Dec
Walk to Beach! King Bed & Free Beach Passes

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings
10.0 out of 10, Exceptional, (48)
"Lovely property."
United States
Melissa W.
The price is AU$363
includes taxes & fees
13 Nov - 14 Nov
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Arnold
10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
United States
Nathan M.
The price is AU$624
includes taxes & fees
11 Nov - 12 Nov
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach
10.0 out of 10, Exceptional, (30)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$649
includes taxes & fees
11 Nov - 12 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"This house could not have a better location. There’s a gorgeous beach right across the street. My family and I spent many hours walking the beach looking for beach glass and shark teeth, which were surprisingly plentiful. There was even a nice dock to fish on. The house is very well kept. The upstairs table on the patio was a favorite of mine. The owner was in constant contact. We had a blast."
United States
Jeff B.
The price is AU$617
includes taxes & fees
8 Dec - 9 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
The price is AU$667
includes taxes & fees
11 Nov - 12 Nov
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge
10.0 out of 10, Exceptional, (14)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is AU$847
includes taxes & fees
16 Nov - 17 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AU$699
includes taxes & fees
17 Nov - 18 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
The price is AU$1,379
includes taxes & fees
6 Dec - 7 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Annapolis Boat Life - Overnight Stays

ANNAPOLIS
10.0 out of 10, Exceptional, (1)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
The price is AU$364
includes taxes & fees
3 Dec - 4 Dec
Annapolis Boat Life - Overnight Stays

Waterfront Getaway, Dock Your Boat & Play!

Edgewater
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 AU$484
includes taxes & fees
11 Nov - 12 Nov
Waterfront Getaway, Dock Your Boat & Play!

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$691
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star
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 favourite 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 depend 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 AU$483 per night. Entering your travel dates in the search wizard might find you 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?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This holiday home rental outside of Cape Anne is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 pool table.

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.