Odyssey Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Odyssey

The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (12)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
United States
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
10.0 out of 10, Exceptional, (31)
"The location is fabulous. We could walk wherever we wanted to go. The room to bathroom ration was also great. We would stay here again. "
United States
Diana L.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
United States
Andrea J.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
United States
Michelle R.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (124)
"Early summer stay and the house, especially the pool, was very clean and tidy. Relaxing and secluded outdoor area with a larger than expected pool for the kids to enjoy. About 0.5 miles to the center of town with excellent restaurants less than 0.25 miles away in Eastport. "
United States
Matthew T.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is NZ$543
includes taxes & fees
3 Nov - 4 Nov
Waterfront Getaway, Dock Your Boat & Play!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (238)
"A great experience all around"
United States
Daniel m.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
9.4 out of 10, Exceptional, (17)
"The gigantic house was perfect for our quick Army-Navy Football game weekend. We hope to come back when it’s warm to take advantage of the great gathering spaces outdoors. Go Navy! Beat Army!!"
United States
Elizabeth B.
The price is NZ$2,019
includes taxes & fees
4 Nov - 5 Nov
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Charming townhome with AC and WiFi in delightful Annapolis
3.0 out of 10, (2)
"So this was the very definition of a flophouse. It is not the whole house, it is not even a secluded room. It was a mattress in the middle of the foyer/entering the kitchen area. The pictures show a nice kitchen - this is where the mattress abuts and again also used by the host. In the pictures the kitchen is clean - in reality there were dirty dishes piled up with some bugs within them; there was also food left on the stove. The area around the house was somewhat sketchy - admittedly we...
United States
Jason
The price is NZ$119
includes taxes & fees
3 Nov - 4 Nov
Charming townhome with AC and WiFi in delightful Annapolis
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (14)
"Beautiful location, great views, beautiful sun rises, view of working watermen Dogwood Harbour. Owner met us at the property with a bottle of wine — very friendly. Tilghman Island is a quaint and beautiful gem."
United States
Frank P.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is NZ$513
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
Fabulous 5-bedroom house with AC in charming Annapolis
2.0 star property
The price is NZ$926
includes taxes & fees
3 Nov - 4 Nov
Fabulous 5-bedroom house with AC in charming Annapolis
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
10.0 out of 10, Exceptional, (111)
"Made a short family trip out of needing to attend a wedding in Baltimore but did not expect how wonderful the trip would be just being in this home. Incredibly family friendly and accommodating for our 11, 10 and not even 1 year old. Very clean, close to amenities and attractions. The hosts were so kind, friendly and accommodating with our needs. "
United States
Hana K.
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Sweet Bamboo Beach Cottage
10.0 out of 10, Exceptional, (82)
"This property is lovely. So close to my daughter it’s a perfect weekend getaway. "
United States
Sheila P.
Sweet Bamboo Beach Cottage
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
The price is NZ$1,591
includes taxes & fees
5 Nov - 6 Nov
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Heated pool, sandy beach, pier, and playground set punch point apart!
10.0 out of 10, Exceptional, (11)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
United States
Jackie C.
Heated pool, sandy beach, pier, and playground set punch point apart!
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
10.0 out of 10, Exceptional, (18)
"Gorgeous views and location. "
United States
Ryan D.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (24)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
United States
Mireia A.
The price is NZ$985
includes taxes & fees
3 Nov - 4 Nov
Edgewater/Mayo Gateaway w/ Hot Tub
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (221)
"Very nice place, we will be visiting again!"
United States
Karen B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Odyssey Hotel Reviews

Find out more about Odyssey

Everything you need to know about Odyssey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Odyssey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Odyssey holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Odyssey holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Odyssey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Odyssey holiday rentals we have selected for you start as low as NZ$119 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Odyssey rentals

At Expedia, we put the best Odyssey holiday 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 Odyssey 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 Odyssey holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Odyssey. 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 holiday rental in Odyssey?

Yes, there are holiday rentals close to the most popular sights in Odyssey, 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 Odyssey has to offer?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of Odyssey is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Odyssey?

While exploring the area, visit family-friendly sights like Chesapeake Beach Water Park, or get outside and enjoy nature at Merkle Wildlife Sanctuary. In the wider area, you’ll find Fridays Creek Winery and Bayside History Museum.

What are holiday rentals like in Odyssey?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Odyssey. Holiday rentals offer extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family getaway.