Annapolis Vacation Rentals from $497: 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 Annapolis WaterVIEW Home : Visitors like this Annapolis vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a 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 .

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

Expedia has 377 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 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.

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

Waterfront Oasis of Annapolis Star

Annapolis

Thomas

$436 nightly

Jul 14 - Jul 15

Total with taxes and fees

Beach nearby, sun loungers, beach towels

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

Arundel on the Bay

Pamela B.

$607 nightly

Jul 13 - Jul 14

Total with taxes and fees

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

$502 nightly

Aug 12 - Aug 13

Total with taxes and fees

Smart TV, fireplace, foosball, table tennis

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

Homewood

Dan B.

$551 nightly

Jul 14 - Jul 15

Total with taxes and fees

Sailboat Experience in Annapolis

Parole

$269 nightly

Jul 13 - Jul 14

Total with taxes and fees

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Cape Saint Claire

KateriK

$671 nightly

Aug 3 - Aug 4

Total with taxes and fees

Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

$440 nightly

Aug 1 - Aug 2

Total with taxes and fees

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Cape Saint Claire

Marissa F.

$615 nightly

Jul 13 - Jul 14

Total with taxes and fees

Charming Annapolis WaterVIEW Home

Arundel on the Bay

Jen M.

$764 nightly

Jul 13 - Jul 14

Total with taxes and fees

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

Stuart P.

$502 nightly

Jul 13 - Jul 14

Total with taxes and fees

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Historic District

$695 nightly

Jul 22 - Jul 23

Total with taxes and fees

Cute bungalow blocks to Stadium

Admiral Heights

Holly W.

$465 nightly

Jul 22 - Jul 23

Total with taxes and fees

Historic Row Home in Downtown Annapolis

Historic District

$497 nightly

Jul 13 - Jul 14

Total with taxes and fees

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Annapolis

$558 nightly

Aug 10 - Aug 11

Total with taxes and fees

Chapel Gate 3BR Steps to City Dock & Naval Academy

Historic District

$474 nightly

Jul 13 - Jul 14

Total with taxes and fees

Upscale Condo in Annapolis w/Private Parking

Historic District

Scott P.

$510 nightly

Aug 12 - Aug 13

Total with taxes and fees

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

Historic District

Brian L.

$559 nightly

Jul 13 - Jul 14

Total with taxes and fees

Luxe Row Home Steps to USNA Gate 3!

Historic District

"Very recent remodel, and all top notch. You can tell the owners put their heart and soul into this property. All the rooms have been very nicely done. Bathrooms were beautifully done. Beds were comfortable. The area is very peaceful and quiet. We really enjoyed the back yard space also. Sat at patio table and used grill. Large TV’s everywhere! We were able to sit at patio table, grill some burgers and watch Final Four games from TV in kitchen area. If you have a Midshipman, this property is...

Brian S.

$1,127 nightly

Jul 22 - Jul 23

Total with taxes and fees

Historic Annapolis Charmer <1Mile to NMC Stadium

Homewood

Susan R.

$1,288 nightly

Aug 11 - Aug 12

Total with taxes and fees

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

Admiral Heights

Jennifer G.

$437 nightly

Jul 19 - Jul 20

Total with taxes and fees

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Top Annapolis Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"This hotel is the best I’ve ever been to. The most extraordinary thing about this hotel is the staff. I would especially like to commend Antoine, Shuttle Driver and Amari at the front desk for going above and beyond their duties to help me during my stay! They are remrkably kind and considerate and I feel grateful to them for their courtesy and kindness! Of most remarkable note is that Amari went out of her way to help me with my reservation and when I offered to tip Antoine for his driver service, he refused to take it, stating that helping me was his pleasure! I was treated like family by everyone from the front desk, the restaurant and pool staff! I thoroughly enjoyed my stay and hope to return soon! I have written a detailed letter to management and hope that a copy of would be placed in their personnel file! These staff members are a true credit to the Hilton group of hotels!"

Historic Inns of Annapolis

8/10 Good

"I loved the room we stayed in. It was clean, well organized, and beautiful. The property itself was also very nice. The only issue was the temperature. The room stayed around 77 degrees, which made it difficult for me to sleep comfortably. We checked in late, and my husband had to be up at 5:00 a.m. the next morning. The front desk offered to move us to another room or send maintenance. By then it was close to midnight, and my husband was already asleep. I wasn't going to wake him up to pack everything and switch rooms, so neither option was really practical. Great staff! At checkout, I mentioned that the room had stayed hot overnight. The front desk apologized and said they would have maintenance look into it. I didn't ask for any compensation, I was tired, still hot, and just wanted to get on the road. Looking back, I think it would have been a nice customer service gesture if management had been notified and offered something like a partial refund or credit for the inconvenience. Overall, the property is beautiful, and we really enjoyed our night. If it hadn't been for the air conditioning issue, it would of been a beautiful stay. I plan on revisiting in the future."

Find out more about Annapolis

Everything you need to know about Annapolis 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 Annapolis 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 Annapolis vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. 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 Annapolis 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 $497 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 Annapolis rentals

At Expedia, we put the best Annapolis 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 Annapolis 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 Annapolis 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 Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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 Annapolis WaterVIEW Home: Visitors like this Annapolis vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a 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 vacation rentals will I find in Annapolis?

Expedia has 377 vacation 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 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

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Check prices for these dates

Our top choices for Annapolis vacation rentals

Waterfront Oasis of Annapolis Star

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

Annapolis Retreat - 7 mins from downtown Annapolis!

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

Sailboat Experience in Annapolis

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Pool Loft Suite | Bay Access & Beach Passes

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Charming Annapolis WaterVIEW Home

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Cute bungalow blocks to Stadium

Historic Row Home in Downtown Annapolis

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Chapel Gate 3BR Steps to City Dock & Naval Academy

Upscale Condo in Annapolis w/Private Parking

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

Luxe Row Home Steps to USNA Gate 3!

Historic Annapolis Charmer <1Mile to NMC Stadium

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

Find vacation rentals that suit your style

Top Annapolis Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

Find out more about Annapolis

Explore a world of travel with Expedia

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