Page 1 of 43
summary and thumbnails  description and thumbnails
Sort By  
Intimidator Fishing Charters | Rock Hall, Maryland | Fishing Trips

Intimidator Fishing Charters

Fishing Trips
Rock Hall, Maryland - 9.2 mi away
Delmarva Balloon Rides | Chester, Maryland | Hot Air Ballooning

Delmarva Balloon Rides

Hot Air Ballooning
Chester, Maryland - 19.6 mi away
The Campgrounds at Sandy Cove | North East, Maryland | Campgrounds & RV Parks

The Campgrounds at Sandy Cove

Campgrounds & RV Parks
North East, Maryland - 25 mi away
The Blue Max Inn | Chesapeake City, Maryland | Bed & Breakfasts

The Blue Max Inn

Bed & Breakfasts
Chesapeake City, Maryland - 27.5 mi away
Sail Selina Ii | Saint Michaels, Maryland | Sailing

Sail Selina Ii

Sailing
Saint Michaels, Maryland - 28.9 mi away
Shore Pedal and Paddle | Saint Michaels, Maryland | Canoe & Kayak Rentals

Shore Pedal and Paddle

Canoe & Kayak Rentals
Saint Michaels, Maryland - 29.2 mi away
Chesapeake Nautical Cruises | Riva, Maryland | Cruises

Chesapeake Nautical Cruises

Cruises
Riva, Maryland - 30.7 mi away
Hike and Explore Assateague Island | Savage, Maryland | Hiking & Trekking

Hike and Explore Assateague Island

Hiking & Trekking
Savage, Maryland - 39.2 mi away
The Cottages Of Governors Run | Port Republic, Maryland | Vacation Rentals

The Cottages Of Governors Run

Vacation Rentals
Port Republic, Maryland - 52.6 mi away
Bedrooms: 2  Sleeps: 4  Bathrooms: 1  
Undersea Outfitters | Westminster, Maryland | Scuba Diving & Snorkeling

Undersea Outfitters

Scuba Diving & Snorkeling
Westminster, Maryland - 55.8 mi away
Chesapeake Bay Scenic Cruises and Tours | Fishing Creek, Maryland | Cruises

Chesapeake Bay Scenic Cruises and Tours

Cruises
Fishing Creek, Maryland - 64.5 mi away
Camp Merryelande Family escapes | Saint George Island, Maryland | Hotels & Resorts

Camp Merryelande Family escapes

Hotels & Resorts
Saint George Island, Maryland - 77.8 mi away
Jet Ski Rentals The Best In Ocean City Maryland. | Ocean City, Maryland | Water Skiing & Jet Skiing

Jet Ski Rentals The Best In Ocean City Maryland.

Water Skiing & Jet Skiing
Ocean City, Maryland - 78.8 mi away
Jacob Rohrbach Inn  - At the Antietam Battlefield | Sharpsburg, Maryland | Bed & Breakfasts

Jacob Rohrbach Inn - At the Antietam Battlefield

Bed & Breakfasts
Sharpsburg, Maryland - 90.1 mi away
Beautiful Weekends or Vacations At 7 C's Lodging | Flintstone, Maryland | Hotels & Resorts

Beautiful Weekends or Vacations At 7 C's Lodging

Hotels & Resorts
Flintstone, Maryland - 136.5 mi away
Maryland Family Kayaking Tours and Snowshoeing | Friendsville, Maryland | Eco Tours

Maryland Family Kayaking Tours and Snowshoeing

Eco Tours
Friendsville, Maryland - 179.3 mi away
SPE Dive School | Chevy Chase, Maryland | Scuba Diving & Snorkeling

SPE Dive School

Scuba Diving & Snorkeling
Chevy Chase, Maryland - 259.1 mi away

Add Your Travel Services and Accommodations

Create a listing on RealAdventures and be seen by millions of travelers making plans for their next vacation.


Top Listings in United States (show all)
Mt. Baker Lodging Cabins At Mount Baker Washington | Maple Falls, Washington | Vacation Rentals

Mt. Baker Lodging Cabins At Mount Baker Washington

Maple Falls, Washington
Vacation Rentals
Africa Tours | Philadelphia, Pennsylvania | Sight-Seeing Tours

Africa Tours

Philadelphia, Pennsylvania
Sight-Seeing Tours
Utah Hot Air Balloon Adventures | Park City, Utah | Hot Air Ballooning

Utah Hot Air Balloon Adventures

Park City, Utah
Hot Air Ballooning
Inn To Inn Hiking On A Slow Adventure | Aptos, California | Hiking & Trekking

Inn To Inn Hiking On A Slow Adventure

Aptos, California
Hiking & Trekking
Hot Springs Cabin Rentals Sequoia Nat'l Monument | California Hot Springs, California | Vacation Rentals

Hot Springs Cabin Rentals Sequoia Nat'l Monument

California Hot Springs, California
Vacation Rentals
Timberpine Lodge Vacation Rental | Adel, Iowa | Vacation Rentals

Timberpine Lodge Vacation Rental

Adel, Iowa
Vacation Rentals
Canoe, kayak and tube the famous Shenandoah River | Luray, Virginia | Kayaking & Canoeing

Canoe, kayak and tube the famous Shenandoah River

Luray, Virginia
Kayaking & Canoeing
Inn to Inn Hiking to San Francisco and Monterey | Aptos, California | Hiking & Trekking

Inn to Inn Hiking to San Francisco and Monterey

Aptos, California
Hiking & Trekking
Maine's Best Vacation Value Poland Spring Resort | Poland Spring , Maine | Hotels & Resorts

Maine's Best Vacation Value Poland Spring Resort

Poland Spring , Maine
Hotels & Resorts
North Country Rivers - Maine Outdoor Adventures | Bingham, Maine | Rafting Trips
Top Listings in North America (show all)
Jeep Wrangler - J. K. Walker Rentals | Halifax, Nova Scotia | Car Rentals

Jeep Wrangler - J. K. Walker Rentals

Halifax, Nova Scotia
Car Rentals
Vancouver Luxury Yacht Charters | Vancouver, British Columbia | Sailing

Vancouver Luxury Yacht Charters

Vancouver, British Columbia
Sailing
Everglades Day Safari | Fort Myers, Florida | Eco Tours

Everglades Day Safari

Fort Myers, Florida
Eco Tours
Your Boatload Of Summer Fun! | Lakehead, California | Cruises

Your Boatload Of Summer Fun!

Lakehead, California
Cruises
Meztli Spanish Language School Tulum | Tulum, Mexico | Language Schools

Meztli Spanish Language School Tulum

Tulum, Mexico
Language Schools
Cielito Lindo Travel Agency Llc | Indio, California | Car & Van Shuttle Service

Cielito Lindo Travel Agency Llc

Indio, California
Car & Van Shuttle Service
Washington Dc's Most Scenic Skydiving Experience | Front Royal, Virginia | Skydiving

Washington Dc's Most Scenic Skydiving Experience

Front Royal, Virginia
Skydiving
Florida Van Rentals - Passenger & Wheelchair Vans | Orlando, Florida | Car Rentals
Wine Country Balloons | Santa Rosa, California | Hot Air Ballooning

Wine Country Balloons

Santa Rosa, California
Hot Air Ballooning


Explore Over 100 Travel Categories To Find Your Next Amazing Vacation

With a diverse array of more than 100 travel categories and options, finding the ideal vacation is a breeze. Whether you are looking for a cozy cabins, luxurious resorts, thrilling adventure tours, or tranquil beach getaways, we have the perfect travel option waiting for you.

  • Bed & Breakfasts
  • Campgrounds & RV Parks
  • Hotels & Resorts
  • Vacation Rentals
  • ATV Riding & Jeep Tours
  • Bike Tours
  • Bungee Jumping
  • Cave Exploration
  • Hang Gliding & Paragliding
  • Hiking & amp;Trekking
  • Horseback Riding & Dude Ranches
  • Hot Air Ballooning
  • Jet Skiing
  • Kayaking & Canoeing
  • Motorcycle Tours
  • Paragliding
  • Rafting Trips
  • Rock Climbing
  • Sailing
  • Scuba Diving & Snorkeling
  • Skydiving
  • Storm Chasing
  • Surfing
  • Tubing
  • Water Parks
  • Water Skiing & Jet Skiing
  • Windsurfing
  • Cruises
  • Yacht Charters
  • Fishing Trips
  • Hunting Trips
  • Fitness & Weight Loss
  • Health Spas & Retreats
  • Spiritual
  • Yoga
  • Adult
  • Arena/Stadium
  • Auto Racing
  • Bars
  • Casinos & Gambling
  • Couples
  • Dance Clubs
  • Educational
  • Go Karting
  • Golf
  • Kids
  • Miniature Golf
  • Monuments
  • Museums
  • Music Venue
  • Night Clubs
  • Parks & Forests
  • Performing Arts
  • Sports Bar
  • Theme Park
  • Tickets
  • Water Parks
  • Birdwatching
  • Camel Riding
  • Eco Tours
  • Llama Trekking
  • Whale Watching
  • Wildlife & Safari Tours
  • Archaeology
  • Artisan & Trade Workshops
  • Cooking Classes & Wine Tasting
  • Cultural Experience
  • Folk Medicine
  • Gold Prospecting
  • Language Schools
  • Museums & Art Galleries
  • Personal Growth
  • Photography Workshops
  • Summer Camps & Programs
  • Survival Training
  • Tennis Lessons
  • Volunteer Vacations
  • Wine Tasting
  • Bicycle Rentals
  • Canoe & Kayak Rentals
  • Car Rentals
  • Jetski & Watercraft Rentals
  • Motorcycle Rentals
  • RV Rentals
  • Sail
  • Sailboat & Yacht Rentals
  • Dog Sledding
  • Skiing & Snowboarding
  • Snowmobiling
  • Snowshoeing
  • X-Country Skiing
  • Scenic Flights
  • Sight-Seeing Tours
  • Train Tours
  • Car & Van Shuttle Service
  • Destination Weddings
  • Passenger Ferry
  • Passport & Visas
  • Reservations
  • Tourism Center
  • Travelers Checks


Top Chestertown, Maryland Vacations & Adventures | Travel Deals & More

Browse the top Chestertown, Maryland vacation travel deals, packages and specials. Make your reservations for the best Chestertown, Maryland adventures, tours, travel, accommodations and much more. Photo gallery, interactive maps, reviews and tips. More Within 5 mi, 10 mi, 25 mi, 50 mi, 100 mi, 250 mi, 500 mi, 1000 mi of Chestertown, Maryland