30a Panama City - Vacation Rentals in Winchester-on-the-Severn

PERFECT LOCATION in the heart of history From US $515
         

10.0 (223 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
All Star Annapolis Retreat - Walk To Stadium From US $589
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Flag House Inn From US $255
         

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9.2 (89 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Luxury Places to Stay in Winchester-on-the-Severn

Over 603+ Luxury Places to Stay in or Near Winchester-on-the-Severn
Waterfront mid-century home From US $2,109
         

New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Annapolis Getaway on the Magothy From US $1,730
         

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New
House
  • Air Conditioner
  • View
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Winchester-on-the-Severn

Over 27+ Top-Rated Vacation Rentals with a Pool in or Near Winchester-on-the-Severn
Annapolis Entertainment Complex From US $743
         

10.0 (95 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Rare find! Chic cottage, salt water heated pool May 15-Oct15. From US $914
         

Annapolis Garden Suite From US $277
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pool Loft Suite | Bay Access & Beach Passes From US $332
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Cool Spring waterfront apartment with pier mins to Annapolis From US $329
         

Pet-Friendly Vacation Rentals in Winchester-on-the-Severn

Over 162+ Pet-Friendly Vacation Rentals in or Near Winchester-on-the-Severn
Historic Row Home 1 Block from Gate 1 at USNA From US $538
         

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9.6 (5 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • View
USNA Luxury Home, parking, pet friendly From US $910
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
New Downtown Annapolis Condo With Free Parking From US $369
         

10.0 (39 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
USNA Home Steps to Stadium Dog-Friendly w Parking From US $725
         

10.0 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic 3 Bedroom Downtown Annapolis Townhome From US $543
         

10.0 (31 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Annapolis Charm –Bright 3BR in Downtown From US $391
         

10.0 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Winchester-on-the-Severn

Over 120+ Large Vacation Homes & Villas in or Near Winchester-on-the-Severn
Charming Annapolis Victorian From US $884
         

10.0 (74 Reviews)
House
  • Air Conditioner
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  • TV
Gaia House From US $126
         

9.3 (59 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10 From US $524
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV

Wheelchair Accessible Vacation Homes in Winchester-on-the-Severn

Over 66+ Wheelchair Accessible Vacation Homes in or Near Winchester-on-the-Severn
Upscale Condo in Annapolis w/Private Parking From US $564
         

1313 West Luxury Boutique Hotel From US $311
         

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10.0 (1 Review)
Hotel
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  • Parking
  • TV
86 State Circle - Luxury Boutique Hotel From US $329
         

10.0 (4 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

Winchester-on-the-Severn Vacation Rentals and Airbnb Places to Stay Under $200

Over 47+ Winchester-on-the-Severn Vacation Rentals and Airbnb Places to Stay Under $200
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! From US $144
         

Entire Private 2 bedrooms house, nice neighborhood From US $194
         

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8.8 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Graduate by Hilton Annapolis From US $198
         

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9.4 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Annapolis waterfront "tiny house" in garden setting From US $171
         

Extended-Stay Annapolis Home Near USNA & Downtown From US $200
         

9.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Winchester-on-the-Severn

Over 296+ Instantly Bookable Vacation Homes in or Near Winchester-on-the-Severn
Cozy 2br home w/parking in downtown Annapolis From US $454
         

Charming Historic Townhouse Steps From USNA From US $312
         

10.0 (41 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
Pristine Downtown 1-Bedroom Steps from State House From US $254
         

About Winchester-on-the-Severn Vacation Rentals

With more than 612 Winchester-on-the-Severn vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, 30apanamacity 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 Winchester-on-the-Severn.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With 30apanamacity Winchester-on-the-Severn, 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 Winchester-on-the-Severn. Places to stay near Winchester-on-the-Severn are 921.64 ft² on average, with prices averaging US $621 a night.

30apanamacity makes it easy and safe to find and compare vacation rentals in Winchester-on-the-Severn 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 Winchester-on-the-Severn

Type Count
Vacation Homes 441
Hotels 67
Holiday Apartments 63
Cottages 14
Villas 4
B&B 2

Use these Quick Filters to Find a Vacation Rental in Winchester-on-the-Severn

Pro Tip: 30apanamacity makes it easy to compare the best listings on 30apanamacity homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between 30apanamacity 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 Winchester-on-the-Severn.

Weather in Winchester-on-the-Severn

View the weather forecast for Winchester-on-the-Severn before booking your Winchester-on-the-Severn 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

Winchester-on-the-Severn Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Winchester-on-the-Severn?
Which vacation homes in Winchester-on-the-Severn are best for families?

If you are looking for a family-friendly vacation home in Winchester-on-the-Severn, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester-on-the-Severn:

How many vacation rentals are available in Winchester-on-the-Severn?

Currently, the total number of properties listed in 2026 is over 612 in the Winchester-on-the-Severn area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winchester-on-the-Severn.