Wander Chesapeake Point
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20 guests
10 beds
4 bathrooms
Game Room•Boat dock•Lake Access
20 guests
7 bedrooms
10 beds
4 bathrooms
6814 sq. ft.
Wander Chesapeake Point is a luxurious waterfront retreat offering an unparalleled escape on the Chesapeake Bay.
The Wander Guarantee
Book with confidence. Read more.
Flexible check-in & out
Check-in after 4:00pm • Check-out before 10:00am • No pets allowed
Easy cancellation
Cancel within 24 hours for a full refund.
Pristine homes, no to-do lists
Arrive to five star cleaning • No chores at checkout • Just lock up and go
About the property
Hotel-grade amenities
Wander is the best of both worlds. The quality of a luxury hotel with the comfort of a private vacation home just for you and your guests.
Common Amenities
- Lake view
- Game Room
- Boat dock
- Wifi
- Free parking
- Hot water
- Fire extinguisher
- Carbon monoxide detector
- Air conditioning
- Balcony
- First aid kit
- Smoke detector
- Patio
Patio
- Lake Access
- Hot tub
- Outdoor seating
- Outdoor dining area
- BBQ Area
- BBQ Utensils
- Fire pit
Living Room 1
- TV
- Fire place
Dining Room
- Dining table
Kitchen
- Oven
- Cooking basics
- Stove
- Microwave
- Freezer
- Fridge
- Dishwasher
- Dishes
- Coffee maker
- Coffee
- Kettle
- Tea
- Spices
- Silverware
- Cleaning supplies
- Wine glasses
Game Room
- TV
- Ping pong table
Bedroom 1
- Bed linens
Ensuite Bathroom 1
- Ensuite bathroom
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Bedroom 2
- Bed linens
Ensuite Bathroom 2
- Ensuite bathroom
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Bedroom 3
- Bed linens
Bedroom 4
- Bed linens
Ensuite Bathroom 3
- Ensuite bathroom
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Bedroom 5
- Bed linens
Bedroom 6
- Bed linens
Bedroom 7
- Bed linens
Half Bath
- Bath linens
- Half bath
- Toilet
- Body soap
Gym
- Gym
- Exercise equipment
Garage
- Air hockey
Laundry Room
- Washer
- Dryer
- Cleaning supplies
Where you’ll sleep
Where you’ll be
Set on over 73 acres of pristine waterfront, this private estate offers unmatched tranquility along the Elk River. Guests can enjoy sweeping water views, a private dock for boating, and even a duck blind for seasonal recreation.
Restaurants
Sonic Drive-In
Sonic Drive-In offers classic American fast food with 100% pure beef burgers, hand-made onion rings, and real ice cream, all served with friendly carhops on roller skates in a nostalgic drive-in setting. It's a fun, quick, and convenient dining experience with a retro vibe.
The Nauti Goose
The Nauti Goose offers savory seafood and refreshing drinks with stunning waterfront views on the North East River, featuring lively weekend entertainment and a welcoming nautical atmosphere perfect for dining, socializing, or special events. Dock your boat and enjoy the vibrant, relaxed vibe year-round.
Schaefer's Canal House
Schaefer's Canal House offers fresh Maryland seafood classics like crab cakes and oysters, served with stunning views of the Chesapeake & Delaware Canal from its cozy dining room and veranda. It's a welcoming waterfront spot perfect for boaters and locals alike.
Chesapeake Inn Restaurant & Marina
Chesapeake Inn Restaurant & Marina offers an upscale waterfront dining experience in historic Chesapeake City, featuring fresh seafood, sushi, and brick-oven pizzas with stunning views of the Chesapeake and Delaware Canal. Its lively deck and elegant dining room make it perfect for casual meals or special occasions.
Wawa
Wawa offers made-to-order hoagies, fresh coffee, and a variety of hot breakfast and dinner options in a casual, 24-hour convenience store setting with ample seating. It’s a beloved East Coast chain known for quick, tasty meals anytime.
Prime 225
Prime 225 offers an elegant dining experience in historic Chesapeake City, featuring the finest prime steaks, fresh seafood, and carefully selected wines in a warm and inviting atmosphere.
UnWined on the Water
UnWined on the Water offers a relaxed waterfront dining experience with a diverse menu of American and seafood dishes, complemented by an extensive wine list and craft cocktails. Its spacious outdoor patio is perfect for enjoying meals with your dog by your side.
Olive Garden Italian Restaurant
Olive Garden offers hearty Italian-American classics in a warm, family-friendly setting, known for its fresh soups, endless breadsticks, and generous portions that bring a comforting taste of Italy to every meal.
The Bayard House Restaurant
The Bayard House Restaurant offers fresh, flavorful seafood in a historic 18th-century setting right on the Chesapeake City waterfront, complete with scenic canal views and a charming, classic ambiance. Its blend of rich history and delicious cuisine creates a memorable dining experience.
Sonny’s Italian Market and Deli
Sonny’s Italian Market and Deli serves up classic Italian-American favorites like award-winning hoagies and cheesesteaks in a welcoming, casual setting that caters to all tastes, including vegetarian options.
Attractions
North East Community Park
North East Community Park offers scenic waterfront views, a playground, picnic pavilions, and the unique Upper Bay Museum showcasing local maritime history. It’s perfect for families, nature lovers, and anyone seeking a peaceful spot to relax or kayak on the North East River.
Woodlands Camping Resort
Woodlands Camping Resort offers a family-friendly getaway with spacious wooded sites, a large swimming pool, playground, and plenty of outdoor activities like hiking and sports courts, perfect for campers seeking relaxation and fun in nature year-round. Veterans are honored here with a special memorial area.
Charlestown Manor Beach And Campground
Charlestown Manor Beach and Campground offers a peaceful waterfront escape with clean facilities, perfect for swimming, kayaking, fishing, and relaxing picnics. It’s ideal for outdoor lovers seeking both adventure and tranquility in a friendly, scenic setting.
Bohemia River State Park
Bohemia River State Park offers peaceful trails through diverse habitats and scenic river views, perfect for nature lovers, bird watchers, and paddlers seeking a quiet outdoor escape. Its gentle terrain and upcoming kayak launch make it ideal for families and beginners.
Brantwood Regional Park
Brantwood Regional Park offers a fun playground with unique swings, slides, and a zip line, plus a paved story trail perfect for families and kids who love adventure and outdoor play. Nature lovers will enjoy the walking paths and nearby pond.
Meadow Park
Meadow Park offers a lively mix of sports courts, a playground, and a community garden perfect for families and active visitors looking to enjoy outdoor fun and fitness in a friendly neighborhood setting.
Elk Neck State Forest
Elk Neck State Forest offers peaceful hiking through diverse trails, birdwatching in a nationally recognized Important Bird Area, and unique outdoor experiences like archery and shooting ranges. Nature lovers and outdoor enthusiasts will enjoy its scenic beauty and variety of activities.
Ben Cardin C&D Canal Trail
The Ben Cardin C&D Canal Trail offers a scenic, paved route along the canal perfect for biking, walking, and wildlife viewing. Ideal for families and outdoor enthusiasts seeking peaceful nature views and easy access to charming Chesapeake City’s shops and eateries.
C & D Canal Museum
The C & D Canal Museum offers a fascinating glimpse into the history and engineering of one of America’s most important sea-level canals, featuring original canal engines and detailed exhibits. History buffs and curious travelers will enjoy exploring this hidden gem in charming Chesapeake City.
Select dates in Wander Chesapeake Point
Choose your check-in & check-out dates
4.9
based on 32 reviews
Guests love the hot tub, private beach and dock with kayaks and water sports, along with stunning waterfront views and a peaceful setting. They praise the spotless, well stocked home, the host's fast communication, and ample space for large family gatherings and a great game room.
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Things to know
Here are some things which you should know before booking Wander Chesapeake Point
Check-in: after 4:00 pm
Check-out: before 10:00 am
20 guests maximum
No pets allowed
No smoking - fees will apply
Events require approval
Cancel within 24 hours for a full refund.
Check-in: after 4:00 pm
Check-out: before 10:00 am
20 guests maximum
No pets allowed
No smoking - fees will apply
Events require approval
Before you book
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Dec 29, 2025 | $1115 | Not Available |
| Dec 30, 2025 | $1067 | Not Available |
| Dec 31, 2025 | $1067 | Not Available |
| Jan 1, 2026 | $1067 | Not Available |
| Jan 2, 2026 | $1067 | Not Available |
| Jan 3, 2026 | $1067 | Not Available |
| Jan 4, 2026 | $950 | Available |
| Jan 5, 2026 | $950 | Available |
| Jan 6, 2026 | $950 | Available |
| Jan 7, 2026 | $950 | Available |
| Jan 8, 2026 | $950 | Available |
| Jan 9, 2026 | $950 | Available |
| Jan 10, 2026 | $950 | Available |
| Jan 11, 2026 | $950 | Available |
| Jan 12, 2026 | $950 | Available |
| Jan 13, 2026 | $950 | Available |
| Jan 14, 2026 | $950 | Available |
| Jan 15, 2026 | $950 | Not Available |
| Jan 16, 2026 | $950 | Not Available |
| Jan 17, 2026 | $950 | Not Available |
| Jan 18, 2026 | $950 | Not Available |
| Jan 19, 2026 | $950 | Not Available |
| Jan 20, 2026 | $950 | Available |
| Jan 21, 2026 | $950 | Available |
| Jan 22, 2026 | $950 | Available |
| Jan 23, 2026 | $950 | Available |
| Jan 24, 2026 | $950 | Available |
| Jan 25, 2026 | $950 | Available |
| Jan 26, 2026 | $950 | Available |
| Jan 27, 2026 | $950 | Available |
| Jan 28, 2026 | $950 | Available |
| Jan 29, 2026 | $950 | Available |
| Jan 30, 2026 | $950 | Available |
| Jan 31, 2026 | $950 | Available |
| Feb 1, 2026 | $980 | Available |
| Feb 2, 2026 | $980 | Available |
| Feb 3, 2026 | $980 | Available |
| Feb 4, 2026 | $980 | Available |
| Feb 5, 2026 | $980 | Not Available |
| Feb 6, 2026 | $980 | Not Available |
| Feb 7, 2026 | $980 | Not Available |
| Feb 8, 2026 | $980 | Not Available |
| Feb 9, 2026 | $980 | Available |
| Feb 10, 2026 | $980 | Available |
| Feb 11, 2026 | $980 | Available |
| Feb 12, 2026 | $980 | Not Available |
| Feb 13, 2026 | $980 | Not Available |
| Feb 14, 2026 | $980 | Not Available |
| Feb 15, 2026 | $980 | Not Available |
| Feb 16, 2026 | $980 | Not Available |
| Feb 17, 2026 | $980 | Available |
| Feb 18, 2026 | $980 | Available |
| Feb 19, 2026 | $980 | Available |
| Feb 20, 2026 | $980 | Available |
| Feb 21, 2026 | $980 | Available |
| Feb 22, 2026 | $980 | Available |
| Feb 23, 2026 | $980 | Available |
| Feb 24, 2026 | $980 | Available |
| Feb 25, 2026 | $980 | Available |
| Feb 26, 2026 | $980 | Available |
| Feb 27, 2026 | $980 | Available |
| Feb 28, 2026 | $980 | Available |
| Mar 1, 2026 | $1067 | Available |
| Mar 2, 2026 | $1067 | Available |
| Mar 3, 2026 | $1067 | Available |
| Mar 4, 2026 | $1067 | Available |
| Mar 5, 2026 | $1067 | Not Available |
| Mar 6, 2026 | $1067 | Not Available |
| Mar 7, 2026 | $1067 | Not Available |
| Mar 8, 2026 | $1067 | Not Available |
| Mar 9, 2026 | $1067 | Not Available |
| Mar 10, 2026 | $1067 | Available |
| Mar 11, 2026 | $1067 | Available |
| Mar 12, 2026 | $1191 | Available |
| Mar 13, 2026 | $1336 | Available |
| Mar 14, 2026 | $1337 | Available |
| Mar 15, 2026 | $1264 | Available |
| Mar 16, 2026 | $1186 | Available |
| Mar 17, 2026 | $1067 | Available |
| Mar 18, 2026 | $1067 | Available |
| Mar 19, 2026 | $1116 | Available |
| Mar 20, 2026 | $1199 | Available |
| Mar 21, 2026 | $1182 | Available |
| Mar 22, 2026 | $1069 | Available |
| Mar 23, 2026 | $1067 | Available |
| Mar 24, 2026 | $1067 | Available |
| Mar 25, 2026 | $1067 | Available |
| Mar 26, 2026 | $1067 | Available |
| Mar 27, 2026 | $1201 | Available |
| Mar 28, 2026 | $1176 | Available |
| Mar 29, 2026 | $1067 | Available |