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Here at VacationHomeRents, you can easily find and compare the best vacation apartments, cabins, house boats, beach houses, and RV deals. By a simple click, we help you search among millions of listings across the top sites like Airbnb, Vrbo, Booking.com and more.
Airbnb Winchester-on-the-Severn, MDVrbo Winchester-on-the-Severn, MDBooking.com Winchester-on-the-Severn, MDOutdoorsy Winchester-on-the-Severn, MDRvshare.com Winchester-on-the-Severn, MD
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ACCOMMODATION TYPES

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Airbnb, Vacation rentals and hotel deals in Winchester-on-the-Severn, MD

Hilton Garden Inn Annapolis
4.1 (2194 reviews)
Hilton Garden Inn Annapolis
Hotel · 1 Bedroom
$159 /night
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Extended Stay America Suites - Annapolis - Admiral Cochrane Drive
3.0 (876 reviews)
Extended Stay America Suites - Annapolis - Admiral Cochrane Drive
Hotel · 1 Bedroom
$90 /night
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Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
3.9 (1528 reviews)
Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
Hotel · 1 Bedroom
$127 /night
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Country Inn & Suites by Radisson, Annapolis, MD
4.3 (2235 reviews)
Country Inn & Suites by Radisson, Annapolis, MD
Hotel · 1 Bedroom
$115 /night
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Sonesta ES Suites Annapolis
4.3 (921 reviews)
Sonesta ES Suites Annapolis
Hotel · 1 Bedroom
$143 /night
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Anchor's Away in the Heart of Eastport!
4.7 (23 reviews)
Anchor's Away in the Heart of Eastport!
Apartment · 2 Guests · 1 Bedroom
$169 /night*
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Chill in this Annapolis Cozy Cottage
5.0 (3 reviews)
Chill in this Annapolis Cozy Cottage
Holiday home · 2 Guests · 1 Bedroom
$146 /night*
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Jode's Retreat "Your home away from home
4.5 (25 reviews)
Jode's Retreat "Your home away from home
Holiday home · 6 Guests · 3 Bedrooms
$185 /night*
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Best Western Annapolis
3.7 (2096 reviews)
Best Western Annapolis
Hotel · 1 Bedroom
$104 /night
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Airbnb, Vacation House with Air Conditioning in Winchester-on-the-Severn, MD

Beautiful, spacious home! 1 mi from USNA! Luxury 3 Bd/3.5 Ba! Private Pool!
Air Conditioning
5.0 (86 reviews)
Beautiful, spacious home! 1 mi from USNA! Luxury 3 Bd/3.5 Ba! Private Pool!
Holiday home · 6 Guests · 3 Bedrooms
$675 /night*
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Waterfront Home with Private Pier
Air Conditioning
5.0 (6 reviews)
Waterfront Home with Private Pier
Holiday home · 8 Guests · 4 Bedrooms
$548 /night*
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Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis:
Air Conditioning
Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis:
Holiday home · 8 Guests · 4 Bedrooms
$350 /night*
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Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Winchester-on-the-Severn, MD

Heart of Downtown, superior location!
Full Kitchen
4.8 (16 reviews)
Heart of Downtown, superior location!
Holiday home · 8 Guests · 4 Bedrooms
$695 /night*
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
Full Kitchen
5.0 (176 reviews)
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Holiday home · 6 Guests · 3 Bedrooms
$345 /night*
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Annapolis-themed home in Downtown Annapolis with Parking
Full Kitchen
5.0 (5 reviews)
Annapolis-themed home in Downtown Annapolis with Parking
Holiday home · 6 Guests · 3 Bedrooms
$329 /night*
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Airbnb, Vacation Cottage with Fireplace in Winchester-on-the-Severn, MD

WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Fireplace
4.9 (34 reviews)
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Cottage · 10 Guests · 5 Bedrooms
$608 /night*
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Private Heated Salt Water Pool, Open and Bright, 5 Stars, 4.5miles DT Annapolis!
Fireplace
5.0 (36 reviews)
Private Heated Salt Water Pool, Open and Bright, 5 Stars, 4.5miles DT Annapolis!
Cottage · 8 Guests · 4 Bedrooms
$599 /night*
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'Newer Cottage Incredibly and Comfortably Furnished.'
Fireplace
4.6 (42 reviews)
'Newer Cottage Incredibly and Comfortably Furnished.'
Cottage · 4 Guests · 2 Bedrooms
$255 /night*
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Airbnb, Pet Friendly Vacation Cottage in Winchester-on-the-Severn, MD

WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Pets Welcome
4.9 (34 reviews)
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Cottage · 10 Guests · 5 Bedrooms
$608 /night*
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What Are The Top Amenities at Winchester-on-the-Severn, MD?

Amenity Info in Winchester-on-the-Severn, MD

The above reveals the top rental amenities and the property numbers associated with each of them in Winchester-on-the-Severn. In Winchester-on-the-Severn, 784 rentals offer Internet or Wifi, 733 rentals offer Air Conditioning, 697 rentals offer No Smoking. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.

How Does The Vacation Home Rental Price Look Like in Winchester-on-the-Severn, MD?

Vacation House & Apartment Rental Price Information in Winchester-on-the-Severn, MD

The graph shows the percentages of vacation homes in each price bucket. Winchester-on-the-Severn has the largest percentage (19.76%) of homes in $500+ price range.
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How Many Accommodations Are Not Pets Friendly in Winchester-on-the-Severn, MD?
Pets Allowed vs Not Allowed in Winchester-on-the-Severn, MD
21.53% of vacation homes in Winchester-on-the-Severn are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
What are the Airports in Winchester-on-the-Severn, MD?
Airports Options in Winchester-on-the-Severn, MD
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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