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Odessa Vacation Rentals

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Check prices for these dates

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Jul 13 - Jul 14
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Jul 14 - Jul 15
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Jul 18 - Jul 20
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Jul 25 - Jul 27

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, (162)
"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, (5)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

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

9.0 out of 10, Wonderful, (4)
"Good experience"
The price is ￥67,670
￥92,671 total
includes taxes & fees
Jul 16 - Jul 17
Charming 2-bedroom cabin close to Fair Hill on horse farm
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, (162)
"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!
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)
"We had a wonderful stay! Really enjoyed the eagles and osprey. The hot tub was amazing and the fire pit was nice to enjoy in the cold weather. All amenities were there that we needed, the location is great and the town is really cute. We will be back! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
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, (51)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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
Ultimate Retreat @ Papermill Rd
Equipped with a microwave, oven, and dishwasher, this kitchen offers a window for natural light and a clean, contemporary design.

Ultimate Retreat @ Papermill Rd

9.0 out of 10, Wonderful, (6)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd
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"
The price is ￥27,864
￥34,574 total
includes taxes & fees
Jul 14 - Jul 15
Nature's Haven Tiny Home
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, (7)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
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, (41)
"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
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Modern kitchen with white cabinetry, black stove, and microwave.

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Luxury 2-bedroom house with Water views, Chesapeake City
Enjoy a scenic view of the lake from this kitchen, featuring a large window and stainless steel appliances.

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (1)
"This is a gorgeous property with a great water view of the canalThe house is beautifully decorated and comfortable, and we loved the upper deck. We had a few issues and Gwen addressed them quickly. The restaurants in town are great and in walking distance. There are interesting areas nearby to explore. "
Luxury 2-bedroom house with Water views, Chesapeake City
Walk to Town & River: Charming Home in North East!
Fridge, microwave, stovetop, dishwasher

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

Walk to Town & River: Charming Home in North East!
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, (19)
"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, (54)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Guest Suite for up to 2 in a Victorian on the Chester River
Stunning two-story home with a gabled roof and inviting front porch.

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (14)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is ￥9,023
￥17,378 total
includes taxes & fees
Jul 15 - Jul 16
Guest Suite for up to 2 in a Victorian on the Chester River
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, (18)
"Everyone in our family ages 8, 10, 17, 18, 38, 64, and 71 thought the house and location were perfect and we had a great stay."
Chesapeake City Quiet Overlook
Beachfront Sunsets on the Water at Oakwood Beach
Relax on the beachside deck with lounge chairs and a covered seating area, steps from the ocean.

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (37)
"We travel in the winter in an RV. We had a friend and nephew who we wanted to spend time with and this house was perfect. The weather was very windy but having the beach right out the door was.perfect motovation to "
Beachfront Sunsets on the Water at Oakwood Beach
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Enjoy meals in the kitchen's dining area with a table and chairs.

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

8.6 out of 10, Excellent, (14)
"Thanks Sean "
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
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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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.