Odyssey Holiday Rentals

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Holiday Rentals in Odyssey

Cottage in North Beach

2.0 star property
10.0 out of 10, Exceptional, (2)
"So comfortable for the 2 of us. Close to restaurants, shopping, liquor store and to family in Chesapeake Beach. The 2nd BR let us spread out suitcases and extras. Stocked kitchen and bath. Grill right out the door to the fenced back yard. Driveway to the door. All we needed and felt at home. "
United States
Patricia M.
The price is AU$427
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Holiday Home in North Beach

10.0 out of 10, Exceptional, (16)
"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.
The price is AU$506
includes taxes & fees
1 Dec - 2 Dec
Walk to Beach! King Bed & Free Beach Passes

Holiday Home in 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 AU$392
includes taxes & fees
1 Dec - 2 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Condo in Historic District

10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
The price is AU$938
includes taxes & fees
8 Dec - 9 Dec
Upscale Condo in Annapolis

Holiday Home in North Beach

10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$675
includes taxes & fees
1 Dec - 2 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Cottage in Owings

10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
The price is AU$421
includes taxes & fees
11 Dec - 12 Dec
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Holiday Home in Prince Frederick

9.6 out of 10, Exceptional, (4)
"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.
The price is AU$563
includes taxes & fees
1 Dec - 2 Dec
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Holiday Home in Arundel on the Bay

9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AU$705
includes taxes & fees
9 Dec - 10 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is AU$662
includes taxes & fees
1 Dec - 2 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Cottage in Benedict

9.2 out of 10, Wonderful, (7)
"The owner was very nice "
United States
karen
The price is AU$442
includes taxes & fees
1 Dec - 2 Dec
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cottage in Stevensville

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is AU$1,366
includes taxes & fees
2 Dec - 3 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Holiday Home in Historic District

10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
The price is AU$477
includes taxes & fees
1 Dec - 2 Dec
Cozy 2br home w/ parking in downtown Annapolis

Holiday Home in Admiral Heights

9.8 out of 10, Exceptional, (6)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is AU$859
includes taxes & fees
1 Dec - 2 Dec
Cute bungalow blocks to Stadium

Holiday Home in Prince Frederick

10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
The price is AU$608
includes taxes & fees
1 Dec - 2 Dec
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Houseboat in Edgewater

The price is AU$4,770
includes taxes & fees
3 Dec - 4 Dec
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Holiday Home in Historic District

10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
The price is AU$1,142
includes taxes & fees
9 Dec - 10 Dec
Historic Row Home 1 Block from Gate 1 at USNA!

Holiday Home in Homewood

9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
The price is AU$713
includes taxes & fees
1 Dec - 2 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Holiday Home in Historic District

10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
The price is AU$957
includes taxes & fees
1 Dec - 2 Dec
Fisher House: Steps From USNA + Covered Parking!

Holiday Home in Homewood

10.0 out of 10, Exceptional, (1)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
The price is AU$1,413
includes taxes & fees
1 Dec - 2 Dec
Stunning 4 BR Home - Walking Distance to Stadium

Holiday Home in Edgewater

10.0 out of 10, Exceptional, (2)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is AU$933
includes taxes & fees
2 Dec - 3 Dec
Golden Anchor Retreat; Lux Living! - Sleeps 7
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, 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 favourite 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 depend 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 AU$392 per night. Entering your travel dates in the search wizard might find you 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.