Book the Best Places to Stay in Annapolis

Find Curated Vacation Rentals, Boutique Cabins, and Stylish Eco-Friendly Acommodation in Annapolis

Charming Apartments in the Heart of Robinson From US $128
         

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9.0 (2 Reviews)
Apartment
  • Air Conditioner
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Country View Inn & Suites From US $138
         

9.2 (287 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Beautifully Restored Farmhouse in Marshall! From US $284
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Comfortable 2BR on the Square From US $298
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy Loft Hideaway in Robinson From US $212
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
2 Bedroom Apartment in the Heart of Robinson From US $77
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Peaceful Robinson Home w/Yard, Near Golf Courses! From US $187
         

The GreyStone House From US $142
         

9.4 (13 Reviews)
House
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Luxury Places to Stay in Annapolis

Over 29+ Luxury Places to Stay in or Near Annapolis
Spacious 3BR on the Square From US $368
         

New
Apartment
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  • TV
Updated Robinson Vacation Rental w/Fireplace! From US $295
         

8.8 (3 Reviews)
Condo
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  • TV
Functional 3 Bedroom Home Near Robinson With WIFI From US $261
         

Updated Robinson Vacation Rental with Fireplace! From US $248
         

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8.0 (1 Review)
Apartment
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Beautifully Restored Farmhouse in Marshall! From US $231
         

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7.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • View
Hike, Boat & Fish: Dog-Friendly Robinson Home From US $191
         

Quaint 1BR with Kitchenette From US $186
         

New
Apartment
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Peaceful Robinson Home with Yard, Near Golf Courses! From US $152
         

Top-Rated Vacation Rentals with a Pool in Annapolis

Over 1+ Top-Rated Vacation Rentals with a Pool in or Near Annapolis
Countryview Inn & Suites From US $138
         

9.5 (68 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Annapolis

Over 3+ Pet-Friendly Vacation Rentals in or Near Annapolis
Hike, Boat and Fish Dog-Friendly Robinson Home From US $143
         

Large Vacation Homes & Villas in Annapolis

Over 1+ Large Vacation Homes & Villas in or Near Annapolis
Private Apartments and Sleeping Rooms Near Marathon, Hershey From US $81
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Sports/Activities

Annapolis Varoom and Airbnb Places to Stay Under $200

Over 14+ Annapolis Varoom and Airbnb Places to Stay Under $200
1 Bedroom Apartment Near Marathon and Hershey From US $141
         

5.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Baymont by Wyndham Robinson From US $115
         

7.0 (257 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
The Robinson Roost
New
From US $131
         

New
House
  • Air Conditioner
  • View
  • Ocean View
Private Queen-Sized Studio Room From US $156
         

10.0 (1 Review)
Apartment
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  • Parking
  • Security/Safety
Private Studio with 2 Full Beds From US $156
         

8.0 (1 Review)
Apartment
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  • Parking
  • Security/Safety
Queen Room with Free Laundry From US $156
         

New
Apartment
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Efficient 2 Story House - 3bed 2bath From US $142
         

Instantly Bookable Vacation Homes in Annapolis

Over 5+ Instantly Bookable Vacation Homes in or Near Annapolis
2BR Apt Right on the Town Square From US $344
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Quiet Annapolis Country House From US $103
         

Private Studio Room with Queen Bed From US $87
         

New
Apartment
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  • Parking
  • Security/Safety

About Annapolis Vacation Rentals

With more than 38 Annapolis vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bettertrips 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 Bettertrips 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 404.22 ft² on average, with prices averaging $173 a night.

Bettertrips 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 18
Holiday Apartments 15
Hotels with Suites 3
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Annapolis

Pro Tip: Bettertrips makes it easy to compare the best listings on Bettertrips homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bettertrips 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