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Deal Island Historic District vacation rentals

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Top-rated vacation rentals in Deal Island Historic District

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Tiny home in Cambridge

4.89 out of 5 average rating, 496 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Jul 6 – 13

G$18,153 GYD per night

Farm stay in Madison

4.98 out of 5 average rating, 163 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Jul 10 – 17

G$25,766 GYD per night

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 293 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Aug 1 – 8

G$17,193 GYD per night

Farm stay in Onancock

4.99 out of 5 average rating, 174 reviews

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Jan 15 – 22

G$37,115 GYD per night

Cottage in California

4.97 out of 5 average rating, 193 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Nov 5 – 12

G$18,502 GYD per night

Cottage in Westover

4.99 out of 5 average rating, 181 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to 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. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Feb 16 – 23

G$70,185 GYD per night

Home in Crisfield

4.95 out of 5 average rating, 254 reviews

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

Nov 25 – Dec 2

G$33,308 GYD per night

Apartment in Lexington Park

5.0 out of 5 average rating, 315 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Nov 10 – 17

G$18,327 GYD per night

Cottage in Onancock

4.97 out of 5 average rating, 195 reviews

Escape to the Eastern Shore - Upscale Waterfront

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles

Sep 1 – 8

G$37,623 GYD per night

Tiny home in Cambridge

4.99 out of 5 average rating, 156 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

Aug 23 – 30

G$22,299 GYD per night

Cottage in Westover

4.92 out of 5 average rating, 142 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

This Chesapeake Bayfront cottage has spectacular views to take you away from everything in any season. It boasts more than 120 feet of waterfront, and you can dangle your feet off the 70 ft “dock of the bay”. Launch kayaks from the small sandy beach in summer, or cozy up to the wood stove in the winter. Inside, you’ll find wood floors throughout, modern kitchen & baths with bay views from every room. Kayaks, SUP, bicycles & crab traps too!

Apr 7 – 14

G$48,704 GYD per night

Villa in Princess Anne

4.83 out of 5 average rating, 120 reviews

Waterfront Retreat & Guest House

Enjoy a relaxing private retreat with an amazing view of the water. Come to stay at the house the whole time enjoying sunsets, kayaking, building sand castles, playing in the water, and making great meals or venture to many nearby towns with great restaurants, hikes, golfing, breweries, bike paths, and more. Enjoy your own private 100 ft pier and sandy beach. **great wifi in main house and guesthouse

Jun 18 – 25

G$183,163 GYD per night

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Popular amenities for Deal Island Historic District vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Deal Island Historic District's top sights

Arby's Dockside Bar and Grill4 locals recommend

Deal Island Boat Ramp3 locals recommend

Arby's General Store4 locals recommend

Other great vacation rentals in Deal Island Historic District

Loft in Lusby

5.0 out of 5 average rating, 311 reviews

Coastal Treetop Retreat w/ Private Beach Access

Sep 18 – 25

G$28,796 GYD per night

Cottage in Heathsville

4.94 out of 5 average rating, 178 reviews

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

Sep 14 – 21

G$25,621 GYD per night

Cottage in White Stone

4.91 out of 5 average rating, 298 reviews

The Moore Cottage

Feb 5 – 12

G$25,073 GYD per night

Home in Reedville

4.96 out of 5 average rating, 203 reviews

Waterfront FamilyFriendly Home Improved for 2023

Apr 5 – 12

G$33,749 GYD per night

Tiny home in Accomac

4.93 out of 5 average rating, 440 reviews

Little Red House on a Farm - Quiet Rural Waterview

Dec 12 – 19

G$25,481 GYD per night

Guest suite in Lusby

4.99 out of 5 average rating, 303 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Mar 16 – 23

G$26,539 GYD per night

Apartment in Church Creek

4.97 out of 5 average rating, 372 reviews

Church Creek Natures' Rest

Nov 7 – 14

G$27,360 GYD per night

Guesthouse in Lusby

4.97 out of 5 average rating, 136 reviews

Cozy Lakeside Studio Retreat.

Jul 30 – Aug 6

G$27,018 GYD per night

Other great vacation rentals in Deal Island Historic District

Guest suite in Deal Island Historic District

4.91 out of 5 average rating, 88 reviews

Private guest suite near Deal Island Maryland

Oct 18 – 25

G$14,275 GYD per night

Camper/RV in Deal Island Historic District

4.86 out of 5 average rating, 14 reviews

Delightful Two Bedroom Camper

Jul 4 – 11

G$18,647 GYD per night

Home in Deal Island Historic District

5.0 out of 5 average rating, 12 reviews

House of the Setting Sun/Deal Island Bayfront Home

Jan 2 – 9

G$44,250 GYD per night

Cottage in Deal Island Historic District

4.96 out of 5 average rating, 69 reviews

Private Beachfront Cottage with 2 Bedrooms + Loft

Oct 5 – 12

G$56,801 GYD per night

Home in Princess Anne

4.86 out of 5 average rating, 7 reviews

Ole Pirate House

Jun 19 – 26

G$24,709 GYD per night

Home in Deal Island Historic District

5.0 out of 5 average rating, 39 reviews

"Promise Point" Bay front home with dock. 3BR 2BA

Dec 31 – Jan 7

G$60,236 GYD per night

Home in Deal Island Historic District

5.0 out of 5 average rating, 20 reviews

Deal Island Lodge

Mar 10 – 17

G$50,978 GYD per night

Home in Crisfield

5.0 out of 5 average rating, 17 reviews

Myrtle Manor- Crisfield Maryland

May 12 – 19

G$31,476 GYD per night

Destinations to explore