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Cape Anne Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Cape Anne vacation rentals

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

1. 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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
$311 nightly
The price is $335
Oct 19 - Oct 20
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

2. 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
$383 nightly
The price is $437
Oct 18 - Oct 19
Total with taxes and fees
3-bedroom house in Deale located on Bay many amenities and great views
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

3. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at this home in North Beach, MD! The house was clean, comfortable, and conveniently located near The Inn at Herrington Harbour, making it a great choice for our visit. Everything worked well for our stay, and we appreciated having a nice place to relax. We would happily recommend this property to anyone looking for a comfortable and convenient place to stay in the area!"
United States
Jeremy P.
$380 nightly
The price is $433
Oct 18 - Oct 19
Total with taxes and fees
Rose Haven Coastal Cottage
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

4. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
$493 nightly
The price is $501
Nov 10 - Nov 11
Total with taxes and fees
Sunset Cottage - West River Access and Views!
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
$272 nightly
The price is $288
Oct 16 - Oct 17
Total with taxes and fees
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A deck with outdoor furniture, a red door, and a house with windows.

6. 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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
$333 nightly
The price is $380
Oct 21 - Oct 22
Total with taxes and fees
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

7. 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, (40 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
$430 nightly
The price is $463
Nov 9 - Nov 10
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$646 nightly
The price is $736
Oct 21 - Oct 22
Total with taxes and fees
Family Home on Mayo Peninsula | Deck | Sleeps 10
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

9. 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, (55 reviews)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
$271 nightly
The price is $292
Oct 19 - Oct 20
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A beach with chairs and a pier in the background.

10. 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.
$473 nightly
The price is $539
Oct 19 - Oct 20
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

11. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$400 nightly
The price is $449
Nov 5 - Nov 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 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.
$505 nightly
The price is $575
Oct 18 - Oct 19
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-Friendly
Pool

13. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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.
$436 nightly
The price is $455
Oct 27 - Oct 28
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

14. 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
$486 nightly
The price is $554
Oct 21 - Oct 22
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

15. 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.
$528 nightly
The price is $602
Nov 3 - Nov 4
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
A calm lake with a sandy shore, surrounded by trees and houses.

16. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
$679 nightly
The price is $774
Oct 18 - Oct 19
Total with taxes and fees
Londontowne Home | Beach | 3BR
A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

17. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
$646 nightly
The price is $736
Oct 18 - Oct 19
Total with taxes and fees
Londontowne Rancher | 3BR | Near Waterfront
Three birds perched on a wooden structure by the water.

18. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
$1,200 nightly
The price is $1,325
Oct 18 - Oct 19
Total with taxes and fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
An outdoor dining area with a wooden table and chairs, a bottle of wine, and a vase of flowers.

19. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
$520 nightly
The price is $574
Oct 16 - Oct 17
Total with taxes and fees
Plum Point Cottage #15
A two-story house with a covered patio, a garage, and a well-maintained lawn.

20. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (55 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
$438 nightly
The price is $499
Oct 19 - Oct 20
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Good"
Ervin 2-night trip
Posted less than an hour ago
Graduate by Hilton Annapolis

Find out more about Cape Anne

Everything you need to know about Cape Anne vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cape Anne vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cape Anne vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cape Anne in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $209 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cape Anne rentals

At Expedia, we put the best Cape Anne vacation 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 vacation.

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 vacation rental in Cape Anne?

Yes, there are vacation rentals close to well known attractions in Cape Anne, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Cape Anne has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Cape Anne vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Cape Anne?

Expedia has 4 vacation 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 Rod n Reel Charter Fishing are a couple of places you'll find in the larger area.

What’s a vacation rental in Cape Anne like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Cape Anne. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for family gatherings.