
Holiday rentals in Janes Island
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Janes Island
Guests agree: these stays are highly rated for location, cleanliness and more.

Pool/HotTub/RecRoom/Pvt. Dock YearRoundPlayground
Discounts Offered! Enjoy best of Eastern Shore living in this unique waterfront retreat offering FULL privacy on 8+ acres! Newly renovated 3BR/2.5BA home blends nature, comfort, & resort‑style amenities PERFECT for families & groups in ALL seasons: *Large Swimming Pool & 7-person Hot Tub *Detached Rec Room w/Pool Tbl *Shaded Outdoor Grill/Sink/Fridge *Private Dock for Fishing/Kayak *W/GOLFING, BEACHES, & HUNTING nearby! Escape the city rushes & don't miss out on Insta-worthy pics! BOOK NOW!!
4.81 out of 5 average rating, 59 reviews
Marshall’s Retreat Chesapeake small town getaway
Modern 3 bedroom home centrally located in the heart of Crisfield, Md. Off & on street parking. Minutes from our towns new bike trail, boat & Kayak launch, park play ground,Wellington Beach, shopping, Ferry’s to The Islands, fishing piers, restaurants, Crab & Cruise (within walking distance), beautiful views. about an hour drive to Ocean City, Assateague or Chincoteague. Or stay in & relax watch Cable tv, Wifi. Please be sure to research the area online to make sure it’s right for your needs.
4.99 out of 5 average rating, 105 reviews
A "True" Chesapeake Bay Waterfront Experience!
Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!
4.94 out of 5 average rating, 191 reviews
Catch of the Bay
Welcome to the completely remodeled catch of the bay cottage! You will enjoy calling this beachy yet rustic location with a farmhouse theme your home during your stay. The home offers three bedrooms and one bathroom - one king bed, one queen bed, and a set of bunkbeds. There’s also a pull out couch if that more so meet your needs. The home offers a remodeled and fully stocked kitchen, laundry area/mudroom on the inside, as well as a spacious backyard, fire pit in front and rear porches.
4.95 out of 5 average rating, 81 reviews
Home of The Terrapin King
The LaVallette House is where the Maryland terrapin originated! Albert Tallmadge LaVallette Jr. launched the terrapin soup industry from this very site in 1887 (you can still see the old terrapin pins beside the driveway). In addition to the property’s historic charm, the location just can’t be beat. The five-bedroom house is completely private. Guests have to drive through wetlands to get to it, and the only neighbors in close proximity are the gulls and the fish in the Chesapeake Bay.
4.81 out of 5 average rating, 42 reviews
Island Time (whole house rental)
3 story home with 2 wrap around porches. One first floor room and three second floor rooms-including a master suite. The third floor is a loft with sleeping for 5 and a full bath. Breathtaking views of sunrises and sunsets. Life on the island is laid back. Visit us to get away from the fast pace life. We offer complimentary bikes, kayaks, fishing poles, crab nets, porch swings, hammock, hot tub, etc. Golf Carts available for rent. Breakfast and STEAMED CRABS are available for a charge.
4.96 out of 5 average rating, 71 reviews
Chesapeake Bay Retreat | Private Dock + Beach
Wake up to sunrises over the creek as you sip your morning coffee and soak in the stillness that surrounds you. 🌿 Outdoor Features: Private dock with multiple boat slips – ideal for crabbing, fishing or just taking in the view Covered porch with a fireplace, tv and gas grill Outdoor fire pit for s’mores in summer or oyster roasts in winter Private beach area for lounging, shell collecting 🎯 Yard Games for All Ages: Hammock for afternoon naps beneath the trees
4.96 out of 5 average rating, 104 reviews
The Serenity House
Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.
4.78 out of 5 average rating, 283 reviews
Rumbley Cottage on the Tangier Sound-Private Beach
September 12-16 available. Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.
4.99 out of 5 average rating, 266 reviews
Marsh View Saxis
With 3 bedrooms and 2 bathrooms, this home offers a perfect blend of comfort and style — and a view you won't get tired of. Watch graceful blue herons wade the wetlands right from your window. Inside, natural light floods the spacious, open living area and kitchen. Outside, the large yard is made for relaxing, with plenty of room to spread out and a fantastic firepit for evenings under the stars.
4.93 out of 5 average rating, 76 reviews
Island Oasis, Tangier Island, Virginia
Island Oasis is a one story, waterfront, newly renovated home situated in the heart of town. The tour boat docks are directly behind property with a gift shop on site. Restaurant, ice cream/sandwich deck, grocery store, church, museum , etc are all within walking distance. Guests will have full access to home and a nice deck overlooking harbor.
5.0 out of 5 average rating, 171 reviews
Cozy Crisfield Cottage
Your family will be close to everything when you stay at this centrally-located cottage located in the heart of Crisfield MD. Minutes away from Wellington Beach, the new bike trail, boat and kayak launch, Crab & Cruise and other attractions. Approximately an hour drive to Ocean City, Assateague and Chincoteague Island.
4.93 out of 5 average rating, 68 reviewsPopular amenities for Janes Island holiday rentals
Other great holiday rentals in Janes Island

Waterfront Family Retreat• Private Dock • 5 BR
4.87 out of 5 average rating, 31 reviews
Waterfront home-225' pier kayak firepit pool beach
5.0 out of 5 average rating, 26 reviews
Deal Island Lodge
5.0 out of 5 average rating, 37 reviews
Eastern Shore Private Sandy Beach & Crabbing dock!
5.0 out of 5 average rating, 12 reviews
Hummingbird Cottage
4.95 out of 5 average rating, 20 reviews
New house, Bay views, 4 Beds, Game room
5.0 out of 5 average rating, 25 reviews
IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental
5.0 out of 5 average rating, 70 reviews
Hope Haven Cottage
5.0 out of 5 average rating, 72 reviewsDestinations to explore
- New York Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
- Jersey City Holiday rentals
- Wilmington Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Richmond Holiday rentals
- Chincoteague Island
- Chesapeake Bay
- Assateague Island National Seashore
- Assateague State Park
- Jolly Roger Amusement Park
- Roland E Powell Convention Center
- Ocean Pines Golf Club
- Ocean City Boardwalk
- Gerry Boyle Park
- Calvert Marine Museum
- Salisbury Zoo
- Trimper Rides of Ocean City
- Ocean City Boardwalk
- Leonardtown Wharf
- NASA’s Wallops Flight Facility Visitor Center
- Suicide Bridge Restaurant
- General's Ridge Vineyard
- Layton's Chance Vineyard and Winery
- Splash Mountain Water Park
- Jolly Roger at the Pier





