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Cape Anne Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Cape Anne holiday rentals

Exterior detail

1. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"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."
United States
Maude H.
The price is HK$1,023
HK$2,614 total
includes taxes & fees
3 Sept - 4 Sept
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Beach nearby

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is HK$669
HK$2,608 total
includes taxes & fees
26 Aug - 27 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Exterior

3. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (54 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is HK$1,133
HK$2,620 total
includes taxes & fees
26 Aug - 27 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Terrace/patio

4. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is HK$1,256
HK$2,862 total
includes taxes & fees
30 Aug - 31 Aug
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Exterior

5. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is HK$1,133
HK$2,687 total
includes taxes & fees
31 Aug - 1 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
Outdoor dining

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

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is HK$1,228
HK$3,804 total
includes taxes & fees
8 Sept - 9 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Smart TV

7. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is HK$2,124
HK$4,558 total
includes taxes & fees
8 Sept - 9 Sept
3-bedroom house in Deale located on Bay many amenities and great views
Interior

8. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is HK$2,140
HK$4,220 total
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!
Marina

9. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,501
HK$3,973 total
includes taxes & fees
26 Aug - 27 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Interior

10. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,561
HK$4,462 total
includes taxes & fees
15 Sept - 16 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
TV, offices

11. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$2,070
HK$5,774 total
includes taxes & fees
27 Aug - 28 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
Coffee/tea maker, fridge, microwave, oven

12. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is HK$1,780
HK$4,728 total
includes taxes & fees
1 Sept - 2 Sept
Renovated Bungalow | Walk to Beach | Dog-Friendly
Outdoor pool, a heated pool

13. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,517
HK$3,106 total
includes taxes & fees
23 Aug - 24 Aug
Waterfront Oasis of Annapolis Star
Pool

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$1,522
HK$4,087 total
includes taxes & fees
21 Sept - 22 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Outdoor dining

15. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (74 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is HK$2,714
HK$5,463 total
includes taxes & fees
21 Sept - 22 Sept
Charming Annapolis WaterVIEW Home
Beach nearby, sun-loungers, beach towels

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,541
HK$5,096 total
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Coffee/tea maker, fridge, microwave, oven

17. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (19 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is HK$671
HK$1,846 total
includes taxes & fees
23 Aug - 24 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access
Coffee/tea maker, fridge, microwave, oven

18. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is HK$1,510
HK$3,831 total
includes taxes & fees
23 Aug - 24 Aug
Pool Loft Suite | Bay Access & Beach Passes
Living area

19. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is HK$1,932
HK$5,071 total
includes taxes & fees
23 Aug - 24 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Exterior

20. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,137
HK$3,639 total
includes taxes & fees
22 Aug - 23 Aug
Plum Point Cottage #17
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

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Front staff checking in and out weren't exactly the friendliest. Very transactional. Not welcoming."
Tina 1-night trip
Posted 7 hours ago
Comfort Inn Conference Center

Find out more about Cape Anne

Search for holiday rentals in Cape Anne on Expedia! You can easily find your home rentals, villas, holiday apartments in Cape Anne using one of the methods below:

  • View our selection of featured holiday rentals in Cape Anne
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  • Enter your travel dates to view the best deals on holiday rentals in Cape Anne while they last

Look no further and take a look at our great range of rental properties in Cape Anne!

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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Cape Anne is located near the beach, and has a fireplace, a balcony 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. It offers a garden, a selection of games 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?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Chesapeake Beach Water Park 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.