Pirate Cove Cottages - Vacation Rentals in Historic District

Walk to Everything - Historic Art’s District From US $493
         

10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • TV
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free From US $703
         

9.8 (38 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Secluded Cozy Cottage in Historic Downtown From US $471
         

9.6 (16 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Walk to everything! Downtown Historic Annapolis “Arts District” From US $700
         

10.0 (5 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Luxury Places to Stay in Historic District

Over 591+ Luxury Places to Stay in or Near Historic District
Nantucket on the Chesapeake Heated Pool From US $2,879
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Annapolis Waterfront From US $2,445
         

9.6 (22 Reviews)
House
  • Air Conditioner
  • Pool
  • TV

Top-Rated Vacation Rentals with a Pool in Historic District

Over 38+ Top-Rated Vacation Rentals with a Pool in or Near Historic District
Waterfront Oasis of Annapolis Star From US $414
         

10.0 (81 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Oasis by the Bay - Waterfront Heated Pool Hot Tub From US $955
         

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10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Annapolis Bayfront Home From US $1,531
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Historic District

Over 153+ Pet-Friendly Vacation Rentals in or Near Historic District
3BR Dog-Friendly Retreat with Fireplace and Patio From US $538
         

10.0 (6 Reviews)
House
  • Parking
  • Pet Friendly
  • Security/Safety
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free From US $848
         

10.0 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free From US $664
         

10.0 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic 3 Bedroom Downtown Annapolis Townhome From US $357
         

10.0 (25 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Tranquility Awaits From US $173
         

10.0 (23 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Historic District

Over 129+ Large Vacation Homes & Villas in or Near Historic District
Charming Annapolis Victorian From US $884
         

10.0 (73 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Pet-Friendly & Spacious Home in Annapolis From US $537
         

Wheelchair Accessible Vacation Homes in Historic District

Over 58+ Wheelchair Accessible Vacation Homes in or Near Historic District
Graduate by Hilton Annapolis From US $225
         

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8.5 (726 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
86 State Circle - Luxury Boutique Hotel From US $308
         

10.0 (3 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

Historic District Varoom and Airbnb Places to Stay Under $200

Over 55+ Historic District Varoom and Airbnb Places to Stay Under $200
Charming Downtown 3rd Floor 1 Bedroom Apt From US $197
         

9.8 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Gaia House From US $126
         

9.3 (55 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Flag House Inn From US $199
         

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9.4 (85 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis From US $182
         

Studio Apartment in Downtown Annapolis From US $182
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Historic District

Over 286+ Instantly Bookable Vacation Homes in or Near Historic District
PERFECT LOCATION in the heart of history From US $404
         

10.0 (217 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy 2br home w/parking in downtown Annapolis From US $371
         

Bay View Studio Apartment From US $314
         

10.0 (59 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Historic District Vacation Rentals

With more than 8 Historic District vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Piratecovecottages 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 Historic District.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages Historic District, 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 Historic District. Places to stay near Historic District are 125 ft² on average, with prices averaging $587 a night.

Piratecovecottages makes it easy and safe to find and compare vacation rentals in Historic District 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 Historic District

Type Count
Cottages 8

Use these Quick Filters to Find a Vacation Rental in Historic District

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

Weather in Historic District

View the weather forecast for Historic District before booking your Historic District 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

Complexes around Historic District, MD