Holiday Rentals in Cape Anne

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Holiday Rentals in Cape Anne

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

10.0 out of 10, Exceptional, (12)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is €516
includes taxes & fees
9 Jul - 10 Jul
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

#2 Egret Cottage Harris Cove

The price is €336
includes taxes & fees
24 Jul - 25 Jul
#2 Egret Cottage Harris Cove

Room for an Island getaway

2.0 star property
9.0 out of 10, Wonderful, (2)
"Was a nice place for the night we were there. It had everything we needed for the night"
The price is €188
includes taxes & fees
30 Jun - 1 Jul
Room for an Island getaway

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

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is €271
includes taxes & fees
2 Jul - 3 Jul
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €252
includes taxes & fees
30 Jun - 1 Jul
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is €1,203
includes taxes & fees
14 Jul - 15 Jul
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is €1,183
includes taxes & fees
14 Jul - 15 Jul
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (1)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
Charming Pet-Friendly Stay - Near Bay & Beaches.

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

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is €394
includes taxes & fees
1 Jul - 2 Jul
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

10.0 out of 10, Exceptional, (1)
"The house is beautiful and on the water. Pool was great. Place was clean. Good communication from hosts. Lovely walking around the neighborhood. Short walk to views of the Bay and mouth of the Severn River. "
The price is €1,153
includes taxes & fees
9 Jul - 10 Jul
Oasis by the Bay - Waterfront Heated Pool Hot Tub!

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is €689
includes taxes & fees
2 Jul - 3 Jul
Charming Cottage with Hot Tub 1 Block from the Bay

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is €559
includes taxes & fees
15 Jul - 16 Jul
Neptune by the Water

Charming Historic Row House in The Heart of Eastport's Horn Point

2.5 star property
10.0 out of 10, Exceptional, (1)
"Gorgeous little house in the heart of Eastport, walking distance to fabulous restaurants and a short hop over the bridge to dwtn Annapolis. The house was clean, well stocked, comfy beds, and the patio was a lovely little oasis to kick back in with a glass of wine at the end of the day. The host was very responsive and accommodating. Highly recommend! "
The price is €535
includes taxes & fees
21 Jul - 22 Jul
Charming Historic Row House in The Heart of Eastport's Horn Point

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is €575
includes taxes & fees
7 Jul - 8 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is €400
includes taxes & fees
30 Jun - 1 Jul
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

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

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is €408
includes taxes & fees
29 Jun - 30 Jun
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is €391
includes taxes & fees
9 Jul - 10 Jul
The Cottage

USNA Luxury Home, parking, pet friendly

10.0 out of 10, Exceptional, (7)
"Beautiful house in a great location to Main Street Annapolis. "
The price is €1,112
includes taxes & fees
29 Jul - 30 Jul
USNA Luxury Home, parking, pet friendly

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (34)
"It was a great place to stay- location, layout and everything else was perfect. Would stay again for sure! "
The price is €636
includes taxes & fees
9 Jul - 10 Jul
Freshly renovated 3-story home 1 block from USNA!

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

9.8 out of 10, Exceptional, (9)
"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 €1,471
includes taxes & fees
30 Jun - 1 Jul
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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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 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.