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Odessa Holiday Rentals

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan

Holiday Rentals in Odessa

Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"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
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

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

9.6 out of 10, Exceptional, (7)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (172)
"Property was in good shape and had plenty of space. Our family loved the beach and the shallow water for the children to play in. Even though we didn’t have perfect weather, we had a wonderful trip."
Chesapeake Bay House with Dock & Private Beach
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Interior

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

9.8 out of 10, Exceptional, (19)
"Clean and comfortable stay in quiet neighborhood! Communication with the host was pleasant and prompt."
The price is HK$1,505
HK$2,592 total
includes taxes & fees
28 Sept - 29 Sept
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Historic Chesapeake City Stay
Marina

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is HK$840
HK$2,168 total
includes taxes & fees
1 Oct - 2 Oct
Historic Chesapeake City Stay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Nancy’s Touch, A Waterfront Paradise!
Terrace/patio

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (169)
"Absolutely fantastic place to stay. When we walked in, it just felt so comfortable. The gardens are beautiful and we were able to see Eagles most every day. Communication was excellent. "
Nancy’s Touch, A Waterfront Paradise!
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (47)
"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
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Terrace/patio

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (2)
"The house is amazing. Very clean and accessible. Carrie and Mike were amazing host . The backyard is truly an oasis. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Tiny Home Tranquil Oasis
Fridge, microwave, oven, stovetop

Tiny Home Tranquil Oasis

The price is HK$1,471
HK$1,880 total
includes taxes & fees
27 Sept - 28 Sept
Tiny Home Tranquil Oasis
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

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

9.8 out of 10, Exceptional, (9)
"From the time we checked in til we checked out was a pleasure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Fair Hill Cabin-10 mins to Newark/UD
Exterior

Fair Hill Cabin-10 mins to Newark/UD

2.0 star property
9.8 out of 10, Exceptional, (8)
"Nice rural setting, close to trails, herd of about 10 deer seen a few times"
Fair Hill Cabin-10 mins to Newark/UD
Cozy loft above ink shop
Fridge, microwave, oven, stovetop

Cozy loft above ink shop

10.0 out of 10, Exceptional, (1)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
The price is HK$580
HK$761 total
includes taxes & fees
5 Oct - 6 Oct
Cozy loft above ink shop
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Marina

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

9.8 out of 10, Exceptional, (6)
"We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO. "
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Stunning waterfront villa with indoor pool and kids swing set and play area.
Spa

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

9.8 out of 10, Exceptional, (18)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

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

10.0 out of 10, Exceptional, (9)
"Great, cozy, quiet little spot! Perfect for 4 adults and a baby. My 1.5 year old loved exploring the deck with an amazing water view, and gained lots of confidence navigating the little steps throughout the house and worked on her balance. Kitchen was well appointed and suited our needs. Would stay here again!"
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Fridge, microwave, oven, stovetop

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.4 out of 10, Exceptional, (9)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Nature's Haven Tiny Home
Terrace/patio

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (3)
"Enjoyed"
The price is HK$1,471
HK$1,825 total
includes taxes & fees
27 Sept - 28 Sept
Nature's Haven Tiny Home
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Fireplace

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.2 out of 10, Wonderful, (12)
"Great location right on the water. Great for fishing or just sitting and relaxing. The house is in a quiet secluded area but only 10 minutes from Chesapeake Bay. Pool was an awesome extra. My son enjoyed it. The home was clean and plenty of space. "
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Dining

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
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

Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

10/10 Excellent
"Amazing gentleman at the front desk. Lovely room."
Lisa 1-night trip
Posted 3 days ago
Best Western Plus Newark/Christiana Inn

Find out more about Odessa

Find out more about Odessa

Search for holiday rentals in Odessa on Expedia! You can easily find your home rentals, villas, holiday apartments in Odessa using one of the methods below:

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Frequently asked questions

Can I find a holiday rental in Odessa?

Yes, there are holiday rentals close to the most popular sights in Odessa, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Odessa has to offer?

Tip Of The Town Fresh and New 3 Bedroom Nest: This holiday home rental outside of Odessa offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 one of the family-friendly sights such as Frightland. Appoquinimink Friends Meeting House and Middletown Town Hall are a couple of places you'll find in the wider area.

What’s a holiday rental in Odessa like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Odessa. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for small groups.