Condo vacation rentals in Crisfield

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Top-rated condo rentals in Crisfield

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Guest favorite

Condo in Heathsville

4.98 out of 5 average rating, 43 reviews

Fleets Cove Farm

Welcome to Fleets Cove Farm y'all! Looking for a peaceful and secluded place to stay? We have the place for you! With expansive fields surrounded by tall hardwood trees, it's hard not to love the light breeze and quiet. At night, sitting around the giant fire pit and looking at the stars is a must. During certain times of the year, you will share the property with pigs and chickens. At request, we can take you to meet our permanent animal residents-mini zebus, our layer chickens, and turkey!

May 31 – Jun 7

$86 per night

Condo in Crisfield

Crisfield Vacation Rental Condo w/ Community Pool!

Memories are waiting to be made at this breezy 3-bedroom, 2-bathroom Crisfield vacation rental. This 5th-floor condo — with a well-stocked kitchen, a fireplace, a screened patio, outdoor dining areas, and access to the community pool and dock — will be the perfect home base for your stay. Laze by the community pool, rent a boat out on the water, and end the day by watching the sunset on your private balcony with a glass of wine. Walk to local restaurants and attractions like Gazebo on The Bay.

Dec 6 – 13

$333 per night

Condo in Crisfield

New place to stay

Crisfield Penthouse Retreat Amazing Water Views!

Escape to our 3-bedroom waterfront condo on the Chesapeake Bay. Enjoy stunning views of Crisfield Harbor from the wrap-around porch and private master bedroom screened porch. Gourmet kitchen, laundry room, and modern amenities ensure comfort. Embark on a fishing excursion, stroll along the picturesque docks, or head to Smith Island for a taste of authentic Chesapeake culture. Whether you're seeking a peaceful retreat or an action-packed adventure on the water, our waterfront condo has it all.

Oct 30 – Nov 6

$150 per night

Guest favorite

Condo in Crisfield

4.88 out of 5 average rating, 17 reviews

Beautiful Waterfront Condo w/ Community Pool!

What better way to start your day than by sitting peacefully on a private balcony with unbeatable bay views while sipping your morning coffee? At this Crisfield vacation rental, those dreams can come true. The 3-bed, 2-bath condo boasts a waterfront location while offering at-home essentials like a fully equipped kitchen and washer and dryer! Entertainment and delicious eateries aren’t far either. Catch a sunset at Crisfield City Dock, then grab a bite of fresh-caught crab down the street!

Jan 25 – Feb 1

$255 per night

Superhost

Condo in Chincoteague

4.72 out of 5 average rating, 18 reviews

An Assateague Adventure

Please give us the opportunity to host you in our modest home drenched in colors inspired by our island sunsets. Located along Eel Creek which feeds into Little Oyster Bay, this 2BR/2BA condo is on the top floor, providing breathtaking marsh views from the condo, and your private side deck to enjoy coffee in the morning or a beverage to close our your evening. Birding paradise. Located on Coach’s Lane at the Assateague Inn- it provides easy pier access for fishing and crabbing.

Aug 5 – 12

$383 per night

Condo in Crisfield

Direct Chesapeake Bay Waterfront Condo

A boating and fishing paradise on the Chesapeake Bay at Harbour Light in Crisfield on the Eastern Shore of Maryland. Crisfield is known as the crabbing capital of the world. This condo is professionally furnished and decorated with high end beach furniture. It is a corner unit on the top floor with a breathtaking 270 degree view. It comes with a 30’ boat slip. Enjoy the view of Tangier and Smith Islands from your balcony view. No pets and no smoking. 1 week minimum rental.

Apr 15 – 22

$300 per night

Guest favorite

Condo in Chincoteague

4.94 out of 5 average rating, 51 reviews

Waterfront Chincoteague Island

Amazing views- Welcome Bird Watchers, Nature and Beach Lovers! Designer condo with direct views of the Intracoastal Waterway Chincoteague Channel and Wallops Long term rental from October-May with government per diem per person and special offers for long term occupancy. Max. occupancy per Chincoteague town fire code is 8. This includes adults, children (2 and older) and infants (children under two). Government ID issued required to be shown on or before check in date.

Nov 12 – 19

$305 per night

Condo in Chincoteague Island

5.0 out of 5 average rating, 3 reviews

Sunset Bay Villas #213

"Another Day in Paradise Chincoteague" Unit 213 has 3 bedrooms, 2 baths, hardwood floors, granite counter tops, beautiful décor, and amazing water views! Sunset Bay Villas is a waterfront community that is a short walk to the Historic Downtown area with shops & restaurants, grocery store, fishing pier, library, and movie theater. Also, the Fireman's Carnival is a short walk away. Great viewing area for 4th of July fireworks in our community's picnic area.

Sep 15 – 22

$350 per night

Superhost

Condo in Chincoteague

4.97 out of 5 average rating, 30 reviews

Sunset Bay Villa 210-Downtown Waterfront Sunsets

Sunset Bay Villa #210 has stylish comfort, beautiful sunset views, seasonal outdoor pool, gym & the perfect downtown location. This professionally decorated condo is on the 2nd Floor (accessible by elevator). The master bedroom enjoys waterfront views and shares deck access with the living room. Fabulous Master bath features jetted tub, separate large shower stall and double sinks. Queen bedroom and twin over double bunk bedroom share full hall bathroom.

Oct 1 – 8

$215 per night

Guest favorite

Condo in Crisfield

4.88 out of 5 average rating, 52 reviews

Crisfield Condo with Spectacular Views

3 BR 2 BA condo with a private boat slip. 1 hour drive to Chincoteague National Wildlife Refuge, Assateague National Seashore, the quaint shops & restaurants of Berlin, MD and Ocean City, MD Beach & Boardwalk. Golf at The Great Hope Golf Course. Enjoy charter fishing, kayaking at Janes Island State Park. Screened in porch with sitting area. Fully equipped kitchen. Full size washer & dryer. Smart TV’s in each bedroom. WIFI ready. All linens are provided.

Nov 27 – Dec 4

$250 per night

Condo in Chincoteague

4.61 out of 5 average rating, 193 reviews

Le Petit Paradis-Waterfront, pet-friendly condo

Le Petit Paradis is our little paradise studio apartment on the Chincoteague Island and we are excited to share it with you! 🏝 Expansive water views, 🌅 gorgeous sunsets, 🐶 pet-friendly policies 🛋 chic furnishings 📱 modern amenities (including WiFi and smart TV) await you at this dream getaway Enjoy your stay in this cozy, newly remodeled studio which overlooks the Chincoteague bay! We welcome pets (no pet fee!)

Apr 16 – 23

$134 per night

Condo in Tangier

New place to stay

The Tarryn Elizabeth Unit A

What better way to enjoy a getaway or family vacation than on a peaceful quiet island where the beach is clean and spacious and some of best fishing and crabbing in the world! Rent a four wheeler and drive on the beach 24/7 or lounge on the porch and soak in the sun, and not to mention the unlimited hi speed Internet with smart TVs in all 3 rooms for all your relaxing needs if you should choose to stay in the home!

Dec 23 – 30

$100 per night