The Best Vacation Rentals - Vacation Rentals in Annapolis

PERFECT LOCATION in the heart of history From US $447
         

10.0 (213 Reviews)
House
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Neptune By The Water From US $991
         

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10.0 (6 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Rare find! Chic cottage, salt water heated pool May 15-Oct15. From US $871
         

Luxury Places to Stay in Annapolis

Over 1252+ Luxury Places to Stay in or Near Annapolis
Stunning Murray Hill gem From US $2,907
         

10.0 (1 Review)
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Nantucket on the Chesapeake Heated Pool From US $2,879
         

10.0 (27 Reviews)
House
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Spacious 6-Bedroom Waterfront Retreat From US $2,071
         

10.0 (2 Reviews)
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Top-Rated Vacation Rentals with a Pool in Annapolis

Over 177+ Top-Rated Vacation Rentals with a Pool in or Near Annapolis
Stunning Waterfront Cottage with Breathtaking Views! From US $449
         

10.0 (220 Reviews)
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Annapolis Entertainment Complex From US $564
         

10.0 (94 Reviews)
House
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  • Pet Friendly
Great Entertaining Spot for any Occassion! From US $513
         

10.0 (91 Reviews)
Cabin
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Waterfront Oasis of Annapolis Star From US $282
         

10.0 (81 Reviews)
Apartment
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Waterfront Annapolis w/swimming pool & pier From US $439
         

10.0 (51 Reviews)
House
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  • Pet Friendly

Pet-Friendly Vacation Rentals in Annapolis

Over 380+ Pet-Friendly Vacation Rentals in or Near Annapolis
Charming Annapolis WaterVIEW Home From US $562
         

9.8 (58 Reviews)
House
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  • Pet Friendly
Pet-Friendly Beach Getaway, Relax by the Bay! From US $267
         

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10.0 (4 Reviews)
Apartment
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  • Pet Friendly
Hilton Garden Inn Annapolis From US $85
         

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8.2 (1006 Reviews)
Hotel
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  • Pet Friendly
Holiday Promo: Get 10% Off Holiday Stays From US $563
         

10.0 (72 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Annapolis

Over 317+ Large Vacation Homes & Villas in or Near Annapolis
Oasis by the Bay - Waterfront Heated Pool Hot Tub From US $955
         

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10.0 (3 Reviews)
House
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  • Pet Friendly
USNA Luxury Home, parking, pet friendly From US $910
         

10.0 (8 Reviews)
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  • Pet Friendly
Charming Annapolis Victorian From US $861
         

10.0 (73 Reviews)
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West Annapolis Cottage From US $883
         

10.0 (35 Reviews)
House
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  • Parking
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Holiday Promo: Get 10% Off Holiday Stays From US $607
         

10.0 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Annapolis

Over 129+ Wheelchair Accessible Vacation Homes in or Near Annapolis
New Downtown Annapolis Condo With Free Parking From US $290
         

10.0 (34 Reviews)
Condo
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  • Pet Friendly
1313 West Luxury Boutique Hotel From US $839
         

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10.0 (1 Review)
Hotel
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86 State Circle - Luxury Boutique Hotel From US $411
         

10.0 (3 Reviews)
Hotel
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  • Wheelchair Accessible
Holiday Promo: Get 10% Off Holiday Stays From US $463
         

10.0 (23 Reviews)
Condo
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  • Pool
The Fritz! - South River Waterfront with Elevator From US $1,255
         

10.0 (1 Review)
House
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Beautiful Condo - Water View Near City Dock From US $157
         

9.6 (154 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Annapolis Varoom and Airbnb Places to Stay Under $200

Over 206+ Annapolis Varoom and Airbnb Places to Stay Under $200
Tranquility Awaits From US $178
         

10.0 (22 Reviews)
Apartment
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  • Pet Friendly
Grandma's Summer House Beverly Beach From US $178
         

10.0 (1 Review)
House
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  • Parking
  • Pet Friendly
Graduate by Hilton Annapolis From US $140
         

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9.4 (1010 Reviews)
Hotel
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Chesapeake Cottage From US $169
         

10.0 (5 Reviews)
Cottage
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  • Parking
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Sailboat Experience in Annapolis From US $200
         

10.0 (1 Review)
Boat Rental
  • Air Conditioner
  • Pet Friendly
  • TV
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! From US $142
         

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis From US $182
         

Instantly Bookable Vacation Homes in Annapolis

Over 637+ Instantly Bookable Vacation Homes in or Near Annapolis
Chesapeake Bay single family home From US $597
         

9.6 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Charming Annapolis WaterVIEW Home From US $896
         

9.6 (51 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Yellow Cottage on Harness Creek From US $307
         

10.0 (170 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Cozy 2br home w/parking in downtown Annapolis From US $311
         

About Annapolis Vacation Rentals

With more than 1261 Annapolis vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Thebestvacationrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Annapolis.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Thebestvacationrentals Annapolis, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Annapolis. Places to stay near Annapolis are 985.47 ft² on average, with prices averaging $558 a night.

Thebestvacationrentals makes it easy and safe to find and compare vacation rentals in Annapolis with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Annapolis

Type Count
Vacation Homes 890
Holiday Apartments 128
Hotels with Suites 124
Cottages 34
Villas 7
B&B 6
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Annapolis

Pro Tip: Thebestvacationrentals makes it easy to compare the best listings on Thebestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thebestvacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Annapolis.

Weather in Annapolis

View the weather forecast for Annapolis before booking your Annapolis Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F