Photo by Kimberly Keegan

Odessa Vacation Rentals

Check prices for these dates

Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Odessa

Chesapeake Bay House with Dock & Private Beach
Relax on the lakeside deck with a round table and four Adirondack chairs, surrounded by a rocky shoreline and a wooden pier.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Guests can enjoy a serene lakeside experience from this picturesque pier, featuring a table and chair for a peaceful retreat.

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

10.0 out of 10, Exceptional, (7)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Historic Chesapeake City Stay
Enjoy waterfront views from the dock and outdoor seating area, situated near a scenic bridge and lush green surroundings.

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
$263 nightly
The price is $279
Aug 6 - Aug 7
Total includes taxes and fees
Historic Chesapeake City Stay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Relax in this stylish living room with a large sofa, armchair, and ottoman, perfect for unwinding in comfort.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a granite countertop.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (19)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

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

9.2 out of 10, Wonderful, (5)
$316 nightly
The price is $335
Aug 25 - Aug 26
Total includes taxes and fees
Charming 2-bedroom cabin close to Fair Hill on horse farm
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Enjoy meals at the central island with a round table and two chairs in this well-equipped kitchen.

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Enjoy serene waterfront views and easy access to boating.

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Walk to Town & River: Charming Home in North East!
Fridge, microwave, stovetop, dishwasher

Walk to Town & River: Charming Home in North East!

10.0 out of 10, Exceptional, (2)
"Great stay and responsive host. So definitely stay again. "
Walk to Town & River: Charming Home in North East!
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Relax in this inviting living space with a comfortable sofa, a cozy bed, and a peaceful atmosphere.

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (9)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Tip Of The Town Fresh and New 3 Bedroom Nest
Modern kitchen with white cabinetry, stainless steel appliances, and a large window.

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (23)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Simple, two-story building with a flat roof, surrounded by trees in a tranquil setting.

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (55)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Enjoy cooking in this well-equipped kitchen with a central island and bench, featuring stainless steel appliances and ample cabinetry.

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (44)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Nancy’s Touch, A Waterfront Paradise!
Stroll through the serene garden, featuring a picturesque arborway, vibrant flowers, and a birdhouse, surrounded by a tranquil body of water.

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (165)
"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..."
Nancy’s Touch, A Waterfront Paradise!
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Relax in a spacious living area with a high ceiling and exposed beams, featuring a large window with an outdoor view, a cozy seating area, and a fireplace.

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.2 out of 10, Wonderful, (11)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Nature's Haven Tiny Home
Enjoy al fresco dining and relaxation on this serene outdoor deck with a barbecue grill and comfortable seating.

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
$226 nightly
The price is $235
Aug 6 - Aug 7
Total includes taxes and fees
Nature's Haven Tiny Home
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Relax in a serene hot tub surrounded by lush greenery and a tranquil view.

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"Great place for a quick getaway - enough room for our family of 4 plus a dog to stay comfortably. Beautiful views! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Comfortable retreat with a bed, mirror, and floral-patterned rug.

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

$286 nightly
The price is $315
Aug 6 - Aug 7
Total includes taxes and fees
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator and black stovetop.

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

8.4 out of 10, Very Good, (6)
"Nice and quiet place to stay"
$288 nightly
The price is $305
Aug 25 - Aug 26
Total includes taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Chesapeake City Quiet Overlook
Enjoy waterfront dining with a view of the bridge spanning the water.

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (20)
"We attended a wedding across the canal from this house at the Chesapeake Inn. It was very cool to see these really large ships go by as we sat on the deck. Very nice accommodations here! Jane was a great host!"
Chesapeake City Quiet Overlook
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

Red Roof Inn PLUS+ Wilmington - Newark

Red Roof Inn PLUS+ Wilmington - Newark

10/10 Excellent
"Clean and good location "
Amr 1-night trip
Posted 1 day ago
Red Roof Inn PLUS+ Wilmington - Newark

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.