Photo by Kimberly Keegan

Odessa Holiday Rentals

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Holiday Rentals in Odessa

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (28)
"This house exceeded our expectations! From the pictures, we knew it would be beautiful, but once we got there it seemed so much bigger and brighter than what the pictures show. Its so light and airy and was perfect for what we came for. It was VERY clean, each bedroom came with towels and makeup wipes. You can tell the hosts put a lot of thought into this home. We went in the fall, but was still such a wonderful time walking along the quiet beach and having drinks on the patio. Would highly...
Beachfront Sunsets on the Water at Oakwood Beach

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Historic home in the heart of Main Street- walkable to shops and restaurants

10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
The price is AU$711
includes taxes & fees
25 Nov - 26 Nov
Historic home in the heart of Main Street- walkable to shops and restaurants

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

9.8 out of 10, Exceptional, (10)
"Couple little things were annoying. Overall a place/property we love. This was our third visit and plan for another."
Stunning waterfront villa with indoor pool and kids swing set and play area.

Ultimate Retreat @ Papermill Rd

8.8 out of 10, Excellent, (5)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AU$797
includes taxes & fees
24 Dec - 25 Dec
Historic Chesapeake City Stay

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook

Clean Sanitized upscale suite. One or two beds. Private Bath

9.8 out of 10, Exceptional, (8)
"David did a great job with everything! Everything I needed was available for me"
The price is AU$223
includes taxes & fees
24 Dec - 25 Dec
Clean Sanitized upscale suite. One or two beds. Private Bath

Beautiful Brick-Wall House in Historic Newcastle

7.6 out of 10, Good, (10)
"The location was ideal considering it was located at a reasonable distances to all places I had to go to. Short or moderate drive to about 5 different locations."
Beautiful Brick-Wall House in Historic Newcastle

Country Get Away 1 Bedroom Apartment

9.8 out of 10, Exceptional, (29)
"We were attending my niece's wedding. Our stay was located in the beautiful countryside yet quick access to places to eat. Our apartment was decorated so cute and for the season. Very, Very clean and I would stay again!"
The price is AU$174
includes taxes & fees
2 Dec - 3 Dec
Country Get Away 1 Bedroom Apartment

Convenient, spacious 3BR 2.5BA WITH PARKING

10.0 out of 10, Exceptional, (1)
"Very nice townhouse close to lots of stores and restaurants."
Convenient, spacious 3BR 2.5BA WITH PARKING

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (59)
"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "
A cottage on the shore of the Delaware River

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (75)
"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Private Carriage House Retreat on a 33 Acre Historic Working Estate

10.0 out of 10, Exceptional, (11)
"Place was great !"
Private Carriage House Retreat on a 33 Acre Historic Working Estate

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

10.0 out of 10, Exceptional, (51)
"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

10.0 out of 10, Exceptional, (33)
"Super clean and beautiful views across the bay."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!

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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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Other types of properties in Odessa you may be interested in

Miller-Dunham House Bed & Breakfast

3.0 star property
10.0 out of 10, Exceptional, (83)
"Exceeded my expectations. I knew that breakfast would be provided each morning. But I didn't know that Jeff is a restaurant chef and his wife Linda is a CIA trained pastry chef. Jeff and Linda were so friendly and accommodating. I felt almost as if I were staying with family. After breakfast I took my 2nd cup of coffee outside to the garden where I read for awhile. There was a sun porch and plenty of outdoor space to accomodate all guests. My partner and I were in the Commander's Room. It was...
The price is AU$327
includes taxes & fees
24 Nov - 25 Nov
Miller-Dunham House Bed & Breakfast

Sonesta Select Newark Christiana Mall

3.0 star property
7.6 out of 10, Good, (1002)
"Relaxing."
The price is AU$178
includes taxes & fees
24 Nov - 25 Nov
Sonesta Select Newark Christiana Mall

Comfort Inn & Suites Newark - Wilmington

2.5 star property
9.0 out of 10, Wonderful, (1011)
"I especially liked the complementary breakfast which offered many choices. I liked that you could get coffee anytime. And fresh lemon infused water was available in the lobby. I also appreciated having a microwave, refrigerator and coffeemaker in my room. Extra pillows on the very comfortable bed were a plus, as was the controllable A/C thermostat. The effective blackout curtains & the quiet were wonderful! All in all, a very favorable experience."
The price is AU$156
includes taxes & fees
24 Dec - 25 Dec
Comfort Inn & Suites Newark - Wilmington
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Beachfront Sunsets on the Water at Oakwood Beach: This holiday home rental outside of Odessa is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 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 Lums Pond State Park 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.