Annapolis Vacation Rentals from ￥29,346: Search Short-Term Rentals

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.

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Our top choices for Annapolis vacation rentals

A waterfront walkway with a brick path, a lamp post, and a bench.

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

Historic District

Nancy N.

￥67,208 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.

￥64,156 total

includes taxes & fees

Nov 9 - Nov 10

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

Historic District

Brian L.

￥80,750 total

includes taxes & fees

Nov 10 - Nov 11

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.

￥77,537 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a brown sofa, a glass coffee table, and a beige armchair.

5. Dean Street's Lower Deck House!

Historic District

Nathaniel R.

￥72,930 total

includes taxes & fees

Nov 9 - Nov 10

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

6. Annapolis Charmer - Perfect Location

Historic District

￥118,390 total

includes taxes & fees

Nov 9 - Nov 10

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.

￥89,952 total

includes taxes & fees

Nov 9 - Nov 10

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

8. Luxe Row Home Steps to USNA Gate 3!

Historic District

Remy S.

￥240,045 total

includes taxes & fees

Nov 9 - Nov 10

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.

￥104,370 total

includes taxes & fees

Nov 9 - Nov 10

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

Historic District

Michael Z.

￥93,758 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.

￥105,412 total

includes taxes & fees

Nov 9 - Nov 10

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.

￥124,458 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.

￥73,279 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a central island, built-in oven, and microwave.

14. Cute bungalow blocks to Stadium

Admiral Heights

Heather B.

￥95,457 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinets, a wooden dining table, and a marble backsplash.

15. Downtown Pinkney House w/Parking

Historic District

Natalie G.

￥104,388 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.

￥87,082 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.

￥88,346 total

includes taxes & fees

Nov 29 - Nov 30

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.

￥87,407 total

includes taxes & fees

Nov 9 - Nov 10

A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

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.

￥83,468 total

includes taxes & fees

Nov 9 - Nov 10

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

20. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport

Stephen P.

￥120,524 total

includes taxes & fees

Nov 9 - Nov 10

View all properties

Find vacation rentals that suit your style

Top Annapolis Hotel Reviews

A white two-story building with a central entrance, a staircase, and a small garden area.

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Excellent

Reyna

A brick building with a large window and a dome in the background.

86 State Circle - Luxury Boutique Hotel

Historic District

10/10 Excellent

MARA

Laurel Grove Inn on the South

Annapolis

10/10 Excellent

Marti

A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

Historic Inns of Annapolis

Historic District

10/10 Excellent

Robert

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Julie

A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

10/10 Excellent

Anonymous traveler

A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.

TownePlace Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Jamila

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

DoubleTree by Hilton Hotel Annapolis

Annapolis

10/10 Excellent

Celina

An outdoor patio with tables, chairs, and a fire feature.

Fairfield Inn & Suites By Marriott Annapolis

Annapolis

10/10 Excellent

Property opened 5/2024. Still pristine when I visited with my fam. Free breakfast was very good. Gym is as you would expect in a Marriott- great. Staff working out some kinks in the check in process. Understandable to me as this is a new team. Nasty surprise when we checked in to learn there was a $30 parking fee. The lot is self park and an open lot. This was not disclosed when I booked on Expedia. I will not return to this property for this reason.

ronald

A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

Sonesta ES Suites Annapolis

Edgewater

10/10 Excellent

This was my first time at this brand of hotel so I didn’t have any expectations. I was surprised in a good way. The room was well appointed for a short stay and very clean. The kitchen was fully stocked. The gym was small but had everything I needed for a couple of workouts. There was also a very well stocked breakfast in the morning. I have special food needs and I found plenty to eat. The entire staff was pleasant and helpful. I had never been there before but will definitely go back.

Sheree

Hilton Garden Inn Annapolis Downtown

Annapolis

10/10 Excellent

Robert

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

Courtyard by Marriott Annapolis

Annapolis

10/10 Excellent

This hotel is incredible, from the service to the amenities. We visit Annapolis to see family every single summer, and this was the first time that we stayed at the Courtyard by Marriott, and it will not be the last. We had some issues with the hotel that we normally stay at, and had to change hotels last minute. We were about 2 hours from Annapolis and were desperate for rooms, and they were more than catering to our needs. We were traveling in a party of five and upon arrival, after hearing...

Lillian

Find out more about Annapolis

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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.

Annapolis Vacation Rentals

Change your mind

Treat yourself

Be picky

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

134 Prince - Luxury Boutique Hotel

10/10 Excellent

Find out more about Annapolis

Frequently Asked Questions

Are there vacation rentals in Annapolis?

What's the top vacation rental in Annapolis?

How many vacation rentals will I find in Annapolis?

What can I see and do in Annapolis?

What are vacation rentals like in Annapolis?