Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Annapolis holiday rentals

Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (83 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$2,122
HK$3,654 total
includes taxes & fees
17 Jun - 18 Jun
Waterfront Oasis of Annapolis Star
Interior

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$1,998
HK$4,730 total
includes taxes & fees
16 Jun - 17 Jun
Annapolis Retreat - 7 mins from downtown Annapolis!
Beach nearby, sun-loungers, beach towels

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, (14 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,962
HK$5,646 total
includes taxes & fees
15 Jun - 16 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Smart TV, fireplace, table football, ping pong

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

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is HK$2,414
HK$4,914 total
includes taxes & fees
15 Jun - 16 Jun
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is HK$1,890
HK$4,072 total
includes taxes & fees
11 Jun - 12 Jun
Charming Annapolis WaterVIEW Home
Property grounds

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.0 out of 10, Wonderful, (13 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is HK$2,998
HK$5,153 total
includes taxes & fees
14 Jun - 15 Jun
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 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$1,669
HK$3,967 total
includes taxes & fees
15 Jun - 16 Jun
Pool Loft Suite | Bay Access & Beach Passes
Microwave, oven, stovetop, dishwasher

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.6 out of 10, Excellent, (4 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is HK$3,238
HK$4,709 total
includes taxes & fees
15 Jun - 16 Jun
Fabulous 5-bedroom house with AC in charming Annapolis
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is HK$3,879
HK$6,334 total
includes taxes & fees
11 Jun - 12 Jun
Secluded Cozy Cottage in Historic Downtown
Living area

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Shower, hair dryer, towels, shampoo

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is HK$2,516
HK$6,295 total
includes taxes & fees
1 Jul - 2 Jul
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Exterior

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, (52 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (81 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is HK$1,967
HK$3,666 total
includes taxes & fees
17 Jun - 18 Jun
Cozy 2br home w/ parking in downtown Annapolis
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,687
HK$2,139 total
includes taxes & fees
18 Jun - 19 Jun
Sailboat Experience in Annapolis
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is HK$1,897
HK$5,250 total
includes taxes & fees
14 Jun - 15 Jun
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Exterior

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is HK$4,178
HK$6,460 total
includes taxes & fees
29 Jun - 30 Jun
Adorable home steps from Navy stadium!
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is HK$1,544
HK$4,503 total
includes taxes & fees
11 Jun - 12 Jun
Historic Row Home in Downtown Annapolis
Smart TV, fireplace, table football, ping pong

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (7 reviews)
"The house was well equipped, clean and comfortable. The host was very accommodating and responsive. This is a great home if you have a large crowd and so convenient to historic Annapolis. "
United States
Susan R.
The price is HK$8,668
HK$14,858 total
includes taxes & fees
29 Jun - 30 Jun
Historic Annapolis Charmer <1Mile to NMC Stadium
Interior

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
The price is HK$3,292
HK$7,045 total
includes taxes & fees
11 Jun - 12 Jun
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Exterior detail

Admiral's Abode - Charming Retreat

Admiral's Abode - Charming Retreat
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Jessica J.
The price is HK$5,564
HK$9,909 total
includes taxes & fees
18 Jun - 19 Jun
Admiral's Abode - Charming Retreat
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 Annapolis Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"The hotel is located not far from the historic district of Annapolis. It is a nice walk towards this area. The hotel staff at the reception are very welcoming. The room is nice. I didn’t like the carpet, but it’s a matter of taste ))) Selection for breakfast is very good and tastes good, but on the second day we had to wait for quite for the food to arrive. Overall, we were very satisfied with our stay and would recommend it to others. Good value for money."
Aida 2-night trip
Posted 12 hours ago
Hilton Garden Inn Annapolis Downtown

Find out more about Annapolis

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

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

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

Frequently asked questions

Are there holiday rentals in Annapolis?

Yes, there are holiday rentals in Annapolis close to Maryland Hall for Creative Arts, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Annapolis speak highly of the university campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What are some of the best holiday rentals that Annapolis has to offer?

Charming Annapolis WaterVIEW Home: This highly rated holiday home rental in Annapolis is located on the waterfront, and has a balcony, 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 dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach.

How many holiday rentals will I find in Annapolis?

Expedia has 384 holiday rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Sandy Point Beach, or simply take in cultural attractions like Annapolis Maritime Museum and Hammond-Harwood House. While here, Maryland State House and William Paca House are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.