Cape Anne Holiday Rentals from NZ$396: Search Short-Term Rentals

Q: 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.

Q: How many holiday rentals will I find in Cape Anne?

Expedia has 4 holiday rentals for your stay in Cape Anne.

Q: 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 wider area.

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Cape Anne holiday rentals

A house with a yellow door and a window with a lamp outside.

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

Deale

Maude H.

includes taxes & fees

7 Sept - 8 Sept

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

2. Sunset Cottage - West River Access and Views!

Shady Side

Marci M.

includes taxes & fees

9 Sept - 10 Sept

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

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

Deale

includes taxes & fees

29 Sept - 30 Sept

A deck with outdoor furniture, a red door, and a house with windows.

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

Shady Side

Joshua T.

includes taxes & fees

21 Sept - 22 Sept

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

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

North Beach

Johanna S.

includes taxes & fees

7 Sept - 8 Sept

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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

North Beach

Penny N.

includes taxes & fees

14 Sept - 15 Sept

A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

7. Rose Haven Coastal Cottage

North Beach

includes taxes & fees

21 Sept - 22 Sept

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

Edgewater

Kristin G.

includes taxes & fees

9 Sept - 10 Sept

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Pamela B.

includes taxes & fees

9 Sept - 10 Sept

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Dawn G.

includes taxes & fees

16 Sept - 17 Sept

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

11. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

16 Sept - 17 Sept

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

Edgewater

Diane D.

A calm lake with a sandy shore, surrounded by trees and houses.

13. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

includes taxes & fees

8 Sept - 9 Sept

A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

14. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

includes taxes & fees

16 Sept - 17 Sept

A bedroom with a sloped ceiling, a bed with a striped bedspread, two red chairs, a television mounted on the wall, and a window with blinds.

15. Annapolis Charmer - Perfect Location

Historic District

includes taxes & fees

8 Sept - 9 Sept

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michelle P.

includes taxes & fees

17 Sept - 18 Sept

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

Chesapeak beach

Bryan P.

includes taxes & fees

7 Sept - 8 Sept

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.

18. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"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. "

rebekah h.

includes taxes & fees

14 Sept - 15 Sept

A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

19. Large 2 bedroom house with private parking in a nice neighborhood

Arnold

Linda B.

includes taxes & fees

7 Sept - 8 Sept

A spacious living room with a large sofa, a coffee table, and a chandelier. There is a kitchen in the background with a dining area.

20. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Homewood

Dan B.

includes taxes & fees

9 Sept - 10 Sept

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Top Cape Anne Hotel Reviews

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Great hotel! Wish the microwave was in the room."

Historic Inns of Annapolis

8/10 Good

"Fantastic location. Clean room with comfortable beds and powerful AC. Liked the history of the building. We were able to consistently get parking on the street near the hotel, which was great. The only real con was that we discovered upon reaching our room that we didn't have an exterior window--our two "windows" looked over the covered event area, which had pretty lights but was nonetheless an interior hallway, so no outside view. There were also a couple hiccups with the bathroom, one being that the glass shelf was falling down, and the other being that we were consistently given two towels even though we had four people on the reservation. But overall we were happy with our stay and appreciated being in a historic building in such a great location."

Sonesta ES Suites Annapolis

8/10 Good

"Ver nice older hotel but well maintained. Spacious rooms and good breakfast. My only complaint is that you can tell they also keep long term tenants as there were cats roaming around (which didn’t bother me but might others) and bikes/trash outside some of the rooms and plants in windows. A normal nightly rental hotel would not allow this id think so it made the atmosphere seem a lil run down even if the room was decent."

Find out more about Cape Anne

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cape Anne holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cape Anne. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cape Anne. Seeing all the best attractions is bound to make you fall in love with Cape Anne. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cape Anne short-term rentals, that won’t be hard to do.

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 Rod n Reel Charter Fishing 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.

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Check prices for these dates

Our top choices for Cape Anne holiday rentals

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

2. Sunset Cottage - West River Access and Views!

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

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

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

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

7. Rose Haven Coastal Cottage

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

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

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

11. Annapolis Retreat - 7 mins from downtown Annapolis!

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

13. Londontowne Home | Beach | 3BR

14. Charming Annapolis WaterVIEW Home

15. Annapolis Charmer - Perfect Location

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

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

18. Londontowne Rancher | 3BR | Near Waterfront

19. Large 2 bedroom house with private parking in a nice neighborhood

20. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Find holiday rentals that suit your style

Top Cape Anne Hotel Reviews

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

Historic Inns of Annapolis

Sonesta ES Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Find out more about Cape Anne

Frequently asked questions

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