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Odessa Vacation Rentals

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Vacation Rentals in Odessa

Beachfront Sunsets on the Water at Oakwood Beach

Salem
10.0 out of 10, Exceptional, (43)
"House was well maintained and very clean. Fantastic view."
United States
Paul P.
Beachfront Sunsets on the Water at Oakwood Beach

Chesapeake Bay House with Dock & Private Beach

Elkton
10.0 out of 10, Exceptional, (177)
"Absolutely love this property! This is my family’s second stay here, we will definitely be coming back. Great hosts, clean house, wonderful location!"
United States
Katie H.
Chesapeake Bay House with Dock & Private Beach

Charming 2-bedroom cabin close to Fair Hill on horse farm

Elkton
9.6 out of 10, Exceptional, (12)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (58)
"Wonderful house in a welcoming, friendly community. "
United States
Benjamin A.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (17)
"Perfect little place for 2. Quiet Very close to Schaefers. "
United States
Karen H.
$263 nightly
The price is $279
Nov 12 - Nov 13
Total with taxes and fees
Historic Chesapeake City Stay

Tiny Home Tranquil Oasis

Bear
$233 nightly
The price is $242
Nov 12 - Nov 13
Total with taxes and fees
Tiny Home Tranquil Oasis

A cottage on the shore of the Delaware River

Salem
9.8 out of 10, Exceptional, (68)
"This small home was perfect for a stay on our road trip. Beautiful views and quiet place to stay."
United States
Taylor A.
A cottage on the shore of the Delaware River

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
9.8 out of 10, Exceptional, (42)
"We stayed for my Birthday! It was definitely a great place to stay. The house was decorated beyond my expectation. We are planing to book again for Girls Weekend."
United States
Billie W.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

2.0 star property
Newark
10.0 out of 10, Exceptional, (3)
"Det var super ophold og god service "
Denmark
Claus R.
$304 nightly
The price is $304
Nov 18 - Nov 19
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Stunning waterfront villa with indoor pool and kids swing set and play area.

Earleville
9.8 out of 10, Exceptional, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
United States
Ann P.
Stunning waterfront villa with indoor pool and kids swing set and play area.

Nature's Haven Tiny Home

Bear
10.0 out of 10, Exceptional, (4)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
$226 nightly
The price is $235
Nov 12 - Nov 13
Total with taxes and fees
Nature's Haven Tiny Home

Sunset River Shack -amazing waterfront view

2.0 star property
Elkton
9.4 out of 10, Exceptional, (3)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
United States
Hope D.
Sunset River Shack -amazing waterfront view

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Elkton
8.8 out of 10, Excellent, (15)
"Lovely place. We really enjoyed our stay"
United States
Renae R.
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Waterfront Lodge packed with Amenities

Earleville
10.0 out of 10, Exceptional, (3)
"Beautiful home. Gorgeous views of Bohemian River. Well maintained House and fully supplied. Our families and friends just loved it. They were already speaking about wanting to return again. "
United States
Virginia G.
Waterfront Lodge packed with Amenities

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Galena
9.8 out of 10, Exceptional, (22)
"Beautiful property overlooking the Sassafras river. Home and property above and beyond pictures. Renter easy to work with and accommodating "
United States
will u.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

House casino

Bear
House casino

Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City
10.0 out of 10, Exceptional, (72)
"This is an exceptional property. The owners have thought of everything. The house is exceptionally clean with updated amenities. Do not hesitate to rent this property."
United States
Sherry D.
Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Nancy’s Touch, A Waterfront Paradise!

North East
10.0 out of 10, Exceptional, (171)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
United States
Buff J.
Nancy’s Touch, A Waterfront Paradise!

Cozy loft above ink shop

Bear
9.4 out of 10, Exceptional, (3)
"Host was extremely responsive, place was in a great location for the lacrosse tournament we played in. Plenty of room, everything was great."
United States
Jeffrey R.
$103 nightly
The price is $107
Nov 12 - Nov 13
Total with taxes and fees
Cozy loft above ink shop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Odessa Hotel Reviews

Find out more about Odessa

Everything you need to know about Odessa vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Odessa vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Odessa vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Odessa vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Odessa. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Odessa in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $107 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Odessa rentals

At Expedia, we put the best Odessa vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Odessa rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Odessa vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Odessa. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Odessa?

Yes, there are vacation rentals near top attractions in Odessa, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Odessa?

Chesapeake Bay House with Dock & Private Beach: Visitors like this Odessa vacation home rental. It is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Odessa?

Explore the area and cultural attractions such as Historic Houses of Odessa, or visit a family-friendly sight such as Frightland. Appoquinimink Friends Meeting House and Middletown Town Hall are a couple of places you'll find in the larger area.

What’s a vacation rental in Odessa like?

A vacation rental is a private property you can stay in for a couple of days or more in Odessa. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for small groups.