Odyssey Vacation Rentals

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Our top choices for Odyssey vacation rentals

9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$261 nightly
The price is $276
Mar 10 - Mar 11
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.0 out of 10, Wonderful, (8 reviews)
"Very nice location. Everything as described. Responsive host."
United States
Michael L.
$239 nightly
The price is $264
Mar 5 - Mar 6
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$293 nightly
The price is $323
Mar 9 - Mar 10
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes

Vacation Home in Waldorf

Haven 2
2.5 star property
$94 nightly
The price is $104
Mar 7 - Mar 8
Total with taxes and fees
Haven 2
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
$423 nightly
The price is $483
Mar 5 - Mar 6
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Vacation Home in Chesapeak beach

Family Beach House: Spacious Deck, Grill & Views
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$417 nightly
The price is $439
Mar 18 - Mar 19
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
$454 nightly
The price is $513
Mar 5 - Mar 6
Total with taxes and fees
Cute bungalow blocks to Stadium
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
$321 nightly
The price is $367
Mar 9 - Mar 10
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$388 nightly
The price is $428
Mar 15 - Mar 16
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
9.6 out of 10, Exceptional, (5 reviews)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
$378 nightly
The price is $401
Mar 30 - Mar 31
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
$421 nightly
The price is $446
Mar 16 - Mar 17
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
$390 nightly
The price is $444
Mar 8 - Mar 9
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
$287 nightly
The price is $327
Mar 24 - Mar 25
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (3 reviews)
"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.
$303 nightly
The price is $345
Mar 15 - Mar 16
Total with taxes and fees
Waterfront Getaway, Dock Your Boat & Play!

Vacation Home in Historic District

Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
$624 nightly
The price is $711
Mar 5 - Mar 6
Total with taxes and fees
Historic Row Home | Hot Tub - 1 Block from Gate 1!
$409 nightly
The price is $434
Mar 5 - Mar 6
Total with taxes and fees
40' Bristol sailboat with spectacular views
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$473 nightly
The price is $539
Mar 17 - Mar 18
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$456 nightly
The price is $520
Mar 11 - Mar 12
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (48 reviews)
"The property was attractive, clean, and comfortable. The host was welcoming and responsive."
United States
Nan J.
$260 nightly
The price is $297
Mar 9 - Mar 10
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (1 review)
$211 nightly
The price is $214
Mar 16 - Mar 17
Total with taxes and fees
Sailboat Experience in Annapolis
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 vacation rentals

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

Odyssey vacation 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 low season months. For more hustle and bustle, you may prefer to visit Odyssey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $104 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Odyssey rentals

At Expedia, we put the best Odyssey vacation 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 vacation.

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 vacation rental in Odyssey?

Yes, we give you a choice of vacation rentals near top local attractions in Odyssey, or you can select a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Odyssey?

Charming Annapolis WaterVIEW Home: This vacation home rental near Odyssey is located on the waterfront and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 larger area, you’ll find Bayside History Museum and Rod n Reel Charter Fishing.

What are vacation rentals like in Odyssey?

Vacation rentals are privately owned accommodations you can book for several days or more in Odyssey. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.