Family-Friendly Hotels in Winchester-on-the-Severn, MD

Booking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family-Friendly Hotels
  3.  USA
  4.  Maryland
  5.  Annapolis
  6.  Winchester-on-the-Severn
Refine your search

Price per night

Amenity Filter

Rating

26 Family-Friendly Hotels in Winchester-on-the-Severn (From $96)

Village Inn Annapolis MD
Village Inn Annapolis MD
Hotel
Annapolis, MD, USA
3.0k from Winchester-on-the-Severn center

Accommodations, Motels, Parking, Pet-friendly, Lodgings, Places to stay, Accessible hotels

6.4

Good

133 reviews

$96
Average price / night
Check Availability
Residence Inn by Marriott Annapolis
Residence Inn by Marriott Annapolis
Hotel
Annapolis, MD, USA
4.0k from Winchester-on-the-Severn center

Accommodations, Parking, Lodgings, Places to stay, Accessible hotels

8.1

Very Good

9 reviews

$169
Average price / night
Check Availability
Fairfield by Marriott Inn & Suites Annapolis
Fairfield by Marriott Inn & Suites Annapolis
Hotel
Annapolis, MD, USA
4.0k from Winchester-on-the-Severn center

Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay, Accessible hotels

8.5

Very Good

53 reviews

$214
Average price / night
Check Availability
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique Hotel
Hotel
Annapolis, MD, USA
4.2k from Winchester-on-the-Severn center

Security/Safety, Bar, Balcony/Terrace, Guest Services, Air Conditioner, Internet, View

5.0

Review score

1 reviews

$695
Average price / night
Check Availability
1313 West Luxury Boutique Hotel
1313 West Luxury Boutique Hotel
Hotel
MD, USA
4.3k from Winchester-on-the-Severn center

Luxury, Accommodations, Parking, 5-star, Lodgings, Places to stay, Family, Accessible hotels

10.0

Exceptional

1 reviews

$839
Average price / night
Check Availability
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
Hotel
Annapolis, MD, USA
4.3k from Winchester-on-the-Severn center

Cheap, Accommodations, Parking, Romantic, Hilton , Pet-friendly, 3-star, Lodgings, Places to stay

8.0

Good

557 reviews

$170
Average price / night
Check Availability
Historic Inns of Annapolis
Historic Inns of Annapolis
Hotel
Annapolis, MD, USA
4.3k from Winchester-on-the-Severn center

Cheap, Accommodations, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.3

Very Good

562 reviews

$300
Average price / night
Check Availability
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
Hotel
Annapolis, MD, USA
4.3k from Winchester-on-the-Severn center

Cheap, Accommodations, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Places to stay, Accessible hotels

8.8

Fabulous

844 reviews

$225
Average price / night
Check Availability
The Westin Annapolis
The Westin Annapolis
Hotel
Annapolis, MD, USA
4.3k from Winchester-on-the-Severn center

Cheap, Accommodations, Pools, Parking, Spa, Romantic, Pet-friendly, 4-star, Lodgings

8.3

Very Good

207 reviews

$207
Average price / night
Check Availability
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
Hotel
Annapolis, MD, USA
4.4k from Winchester-on-the-Severn center

Cheap, Accommodations, Pools, Parking, 3-star, Lodgings, Places to stay, Accessible hotels

8.3

Very Good

485 reviews

$145
Average price / night
Check Availability
Capital Hotel Annapolis
Capital Hotel Annapolis
Hotel
Winchester-on-the-Severn, Annapolis, Maryland, USA
4.4k from Winchester-on-the-Severn center

Air Conditioner, Breakfast, Child Friendly

9.7

Exceptional

3 reviews

$279
Average price / night
Check Availability
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
Hotel
Winchester-on-the-Severn, Annapolis, Maryland, USA
4.5k from Winchester-on-the-Severn center

Luxury, Accommodations, Parking, 5-star, Lodgings, Places to stay

9.8

Exceptional

26 reviews

$1314
Average price / night
Check Availability
Gibson's Inn at Gate One
Gibson's Inn at Gate One
Hotel
Annapolis, MD, USA
4.6k from Winchester-on-the-Severn center

Entertainment, Business Services, Wheelchair Accessible, Sports/Activities, Wellness Facilities, Breakfast, Smoking

New to Booking
$435
Average price / night
Check Availability
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHG
Hotel
Annapolis, MD, USA
4.7k from Winchester-on-the-Severn center

Accommodations, Parking, Romantic, Holiday inn , 3-star, Lodgings, Places to stay, Family, Accessible hotels

7.4

Good

217 reviews

$103
Average price / night
Check Availability
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
Hotel
Annapolis, MD, USA
4.8k from Winchester-on-the-Severn center

Accommodations, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Places to stay, Accessible hotels

8.2

Very Good

128 reviews

$332
Average price / night
Check Availability
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
Hotel
Annapolis, MD, USA
5.0k from Winchester-on-the-Severn center

Accommodations, Pools, Parking, Boutique, Pet-friendly, 4-star, Lodgings, Places to stay, Accessible hotels

8.0

Good

345 reviews

$149
Average price / night
Check Availability
Red Roof Inn Annapolis
Red Roof Inn Annapolis
Hotel
Annapolis, MD, USA
5.2k from Winchester-on-the-Severn center

Accommodations, Motels, Parking, Pet-friendly, Lodgings, Places to stay, Accessible hotels

6.1

Good

303 reviews

$116
Average price / night
Check Availability
Best Western Annapolis
Best Western Annapolis
Hotel
Annapolis, MD, USA
5.2k from Winchester-on-the-Severn center

Accommodations, Pools, Parking, Best western , Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

7.3

Good

575 reviews

$130
Average price / night
Check Availability
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
Hotel
Annapolis, MD, USA
5.4k from Winchester-on-the-Severn center

Cheap, Accommodations, Pools, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Hot tubs

8.5

Very Good

844 reviews

$137
Average price / night
Check Availability
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis
Hotel
Annapolis, MD, USA
5.6k from Winchester-on-the-Severn center

Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Places to stay, Family, Accessible hotels

7.2

Good

473 reviews

$145
Average price / night
Check Availability
Candlewood Suites Annapolis by IHG
Candlewood Suites Annapolis by IHG
Hotel
Annapolis, MD, USA
5.8k from Winchester-on-the-Severn center

Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering, Accessible hotels

8.5

Very Good

153 reviews

$123
Average price / night
Check Availability

Pro Tip for Travelers:
HotelsWithSuites simplifies your search by aggregating premium inventory from global leaders like Booking.com, Expedia, and Vrbo. Whether you need oceanfront hotels, a private pool, or a pet-friendly suite, use our Advanced Filters to instantly compare the top-rated Family-Friendly Hotels in Winchester-on-the-Severn.

Stay Near Winchester-on-the-Severn's Top Attractions

HotelsWithSuites can help you find hotels, resorts, and suites near many of 's top attractions, neighborhoods, and points of interest.

Winchester-on-the-Severn Family-Friendly Hotels on the Map

Frequently Asked Questions

Family-friendly hotels in Winchester-on-the-Severn often offer spacious rooms, kid-friendly amenities, and on-site activities. Features like pools, play areas, and family suites can make your stay more comfortable.

Yes, you can find 26 family-friendly hotels in Winchester-on-the-Severn with prices starting from around $96 per night, depending on travel dates and room size.

Many properties cater to families with services such as babysitting, kids’ clubs, or child-friendly dining options. Availability may vary by hotel.

Booking early is recommended during school holidays and peak travel seasons. This ensures better room availability and access to family-oriented amenities.

Yes, many family-friendly hotels in Winchester-on-the-Severn offer connecting rooms, suites, or multi-bedroom accommodations designed for larger groups.