Annapolis Vacation Rentals from CA $548: Short-Term Rentals for 2026

Q: Are there vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Maryland Hall for Creative Arts, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists who visit Annapolis speak highly of the college campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

Q: What's the top vacation rental in Annapolis?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach : Visitors like this Annapolis 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. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital .

Q: How many vacation rentals will I find in Annapolis?

Expedia has 381 vacation rentals for your stay in Annapolis.

Q: What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Bay Ridge 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.

Q: What are vacation rentals like in Annapolis?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Annapolis. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for families.

Check prices for these dates

In two weeks

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Our top choices for Annapolis vacation rentals

A wooden dock extending into a calm body of water with boats docked at the end.

1. Cozy 2br home w/ parking in downtown Annapolis

Historic District

Nancy N.

CA $596 total

includes taxes & fees

Nov 30 - Dec 1

A kitchen with a wooden countertop, a stove, and a refrigerator.

2. 18th Cent. Charm in Historic Downtown Annapolis

Historic District

Bradford R.

CA $548 total

includes taxes & fees

Nov 8 - Nov 9

3. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Historic District

Brian L.

CA $688 total

includes taxes & fees

Nov 9 - Nov 10

A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

4. Upscale Condo in Annapolis w/Private Parking

Historic District

Scott P.

CA $709 total

includes taxes & fees

Nov 17 - Nov 18

A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

5. Dean Street's Lower Deck House!

Historic District

Nathaniel R.

CA $647 total

includes taxes & fees

Nov 10 - Nov 11

A dining area with a wooden table, chairs, a chandelier, and a clock on the wall.

6. Annapolis Charmer - Perfect Location

Historic District

CA $1,042 total

includes taxes & fees

Nov 10 - Nov 11

A living room with a dining table, two sofas, a coffee table, and a patterned rug.

7. Chapel Gate 3BR Steps to City Dock & Naval Academy

Historic District

JENNIFER E.

CA $775 total

includes taxes & fees

Nov 10 - Nov 11

A patio with a brick floor, outdoor furniture, and a grill.

8. Luxe Row Home Steps to USNA Gate 3!

Historic District

Remy S.

CA $2,123 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a fireplace, a television mounted above it displaying an airplane, and a glass coffee table.

9. 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

Michaell M.

CA $896 total

includes taxes & fees

Nov 10 - Nov 11

10. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic District

Michael Z.

CA $829 total

includes taxes & fees

Nov 10 - Nov 11

A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

11. Historic Row Home in Downtown Annapolis

Historic District

Amy T.

CA $932 total

includes taxes & fees

Nov 16 - Nov 17

A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

12. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Historic District

Rosie G.

CA $1,110 total

includes taxes & fees

Nov 9 - Nov 10

Stylish kitchen with open layout and island seating

13. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

CA $653 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living room with a sofa, armchairs, and a coffee table. There is a large window with curtains, a door, and a mirror on the wall.

14. Cute bungalow blocks to Stadium

Admiral Heights

Heather B.

CA $844 total

includes taxes & fees

Nov 10 - Nov 11

A narrow street lined with wooden houses, some with visible front porches and steps leading to the entrance.

15. Downtown Pinkney House w/Parking

Historic District

Natalie G.

CA $931 total

includes taxes & fees

Nov 9 - Nov 10

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.

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

Homewood

Dan B.

CA $776 total

includes taxes & fees

Nov 11 - Nov 12

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

17. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

CA $784 total

includes taxes & fees

Nov 17 - Nov 18

A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

18. Mins to Historic Downtown Annapolis - Parking

Annapolis

Nader E.

CA $772 total

includes taxes & fees

Nov 9 - Nov 10

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

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

Annapolis

"A nice, clean, roomy place at a good price--gotta love that. The walk-out basement apartment was located in a compound of units on a quiet dead-end street. This unit is actually toward the back and I spent a little time searching for it. Once there, access to the key and apartment was no problem.The home was well-stocked with kitchen and bathroom supplies, and bedding. Would definitely stay there again."

Rob L.

CA $738 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

20. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport

Stephen P.

CA $1,066 total

includes taxes & fees

Nov 10 - Nov 11

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Top Annapolis Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"Would have loved water in the room."

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"The last time I inquired the rate was extremely too high for the same room. But this time the rate was reasonable. it is a shame that when the military families come to visit their relatives the prices are jacked up! As military (34yrs) retiree, that is repulsive! This is my favorite hotel!"

SpringHill Suites by Marriott Annapolis

8/10 Good

"The staff was very helpful & accommodating when we expressed our concerns. We had booked this stay as an in between stop on our long vacation & mainly booked it because it had an indoor pool the kids could use for the few days in the middle. We also were unaware there is a parking fee of 8 dollars every night you stay. We did leave a night early simply because the pool was closed for the weekend. When we arrived it was closed & we were told it would be closed all weekend but was open around 9 at night & filled with people. It was open again when we walked by around 2pm the next day with people in it once again. So we got dressed & went down to get in & it was once again closed & we were told again it was closed all weekend for maintenance. After the disappointment from the kiddos & the extra money I paid for a pool specifically ( not to mention the nightly parking fee ) we decided to leave early & just continue our driving travels. The front desk was very understanding & kind. They also offered to refund me a night even though we hadn’t decided to leave until 2pm the day before checking out. So that was very nice & I know the inconveniences were not the responsibility of the staff! Over all it was a great hotel room, comfy beds, & very nice stuff. Only issues were the pool, the lack of information regarding it & the parking fee."

Find out more about Annapolis

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Annapolis. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Maryland Hall for Creative Arts, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists who visit Annapolis speak highly of the college campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What's the top vacation rental in Annapolis?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Annapolis 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. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital.

How many vacation rentals will I find in Annapolis?

Expedia has 381 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Bay Ridge 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 vacation rentals like in Annapolis?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Annapolis. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for families.

Room 1

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Treat yourself

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Check prices for these dates

Our top choices for Annapolis vacation rentals

1. Cozy 2br home w/ parking in downtown Annapolis

2. 18th Cent. Charm in Historic Downtown Annapolis

3. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

4. Upscale Condo in Annapolis w/Private Parking

5. Dean Street's Lower Deck House!

6. Annapolis Charmer - Perfect Location

7. Chapel Gate 3BR Steps to City Dock & Naval Academy

8. Luxe Row Home Steps to USNA Gate 3!

9. 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.

10. Historic Row Home | Hot Tub - 1 Block from Gate 1!

11. Historic Row Home in Downtown Annapolis

12. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

13. Pool Loft Suite | Bay Access & Beach Passes

14. Cute bungalow blocks to Stadium

15. Downtown Pinkney House w/Parking

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

17. Annapolis Retreat - 7 mins from downtown Annapolis!

18. Mins to Historic Downtown Annapolis - Parking

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

20. Eastport 3 bedroom Cottage: Walk to Downtown

Find vacation rentals that suit your style

Top Annapolis Hotel Reviews

Graduate by Hilton Annapolis

Crowne Plaza Annapolis by IHG

Hilton Garden Inn Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis Waterfront Hotel, Autograph Collection

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

SpringHill Suites by Marriott Annapolis

Find out more about Annapolis

Frequently asked questions

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