Holiday Rentals in Odyssey

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Holiday Rentals in Odyssey

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District
10.0 out of 10, Exceptional, (33)
"Our stay was AMAZING! Perfect location, plenty of space! Will definitely book again when we have a larger group like we did for PPW! "
United States
Charolene P.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
Stevensville
6.4 out of 10, (7)
"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

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Historic District
10.0 out of 10, Exceptional, (124)
"This house is in a wonderful location relative to town and the Naval Academy. The house is lovely and was very comfortable for all 6 of us. Clean, spacious, and great bedding. The garden is beautiful. Arranging for parking on the street was great."
United States
cara
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (19)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
United States
Kerry G.
The price is €1,026
includes taxes & fees
2 Dec - 3 Dec
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Waterfront Getaway, Dock Your Boat & Play!

Edgewater
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.
Waterfront Getaway, Dock Your Boat & Play!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Eastport
10.0 out of 10, Exceptional, (125)
"We had a great stay! The house was adorable and the pool was awesome!"
United States
Kathleen J.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
9.8 out of 10, Exceptional, (50)
"Our week at Jacob's property was excellent. It was the perfect location for a family getaway, and Jacob was helpful and responsive."
United States
Brett F.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (24)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
Edgewater/Mayo Gateaway w/ Hot Tub

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic
10.0 out of 10, Exceptional, (124)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Port Republic
10.0 out of 10, Exceptional, (181)
"Everything about this cabin was just what we were looking for! From the initial booking until we left we were taken care of by Brett. The pictures on-line were spot on but seeing the bay view in person from the windows and deck took my breath. There was a lot to do and we took advantage of close by activities (hiking, paddle-boarding, kayaking, jet skiing) but the cabin is a destination in itself with it's peaceful and calm surroundings. We were blessed with beautiful sunrises, hummingbirds and...
United States
Vicki K.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Walk to the stadium! - Lighthouse on Glenwood

Annapolis
10.0 out of 10, Exceptional, (5)
The price is €343
includes taxes & fees
30 Nov - 1 Dec
Walk to the stadium! - Lighthouse on Glenwood

The Blue Crab Beach House - Free beach passes

North Beach
10.0 out of 10, Exceptional, (76)
"Excellent communication and place "
United States
Desiree
The Blue Crab Beach House - Free beach passes

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
Murray Hill
10.0 out of 10, Exceptional, (34)
"Absolutely perfect! Will stay again!!"
United States
Brian
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Fabulous 5-bedroom house with AC in charming Annapolis

2.0 star property
Annapolis
The price is €469
includes taxes & fees
3 Dec - 4 Dec
Fabulous 5-bedroom house with AC in charming Annapolis

Million Dollar View of the Chesapeake Bay

Deale
9.8 out of 10, Exceptional, (130)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of the Chesapeake Bay

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is €235
includes taxes & fees
1 Dec - 2 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville
10.0 out of 10, Exceptional, (56)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sherwood
10.0 out of 10, Exceptional, (20)
"Fantastic property"
United States
Harvey W.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
9.6 out of 10, Exceptional, (21)
"Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay."
United States
Kristin A.
Bay views with kayaks, bikes, fire pit, crabbing and more

Fisher House: Steps From USNA + Covered Parking!

Historic District
10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
The price is €561
includes taxes & fees
1 Dec - 2 Dec
Fisher House: Steps From USNA + Covered Parking!
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 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, apart-hotels, 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 €235 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?

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This holiday home rental outside of Odyssey is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Shadyside Park. In the wider area, you’ll find Rod n Reel Charter Fishing and Chesapeake Beach Railway 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.