Odyssey Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Odyssey

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

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 HK$613
HK$2,026 total
includes taxes & fees
1 Dec - 2 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes

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 HK$664
HK$2,554 total
includes taxes & fees
1 Dec - 2 Dec
Walk to Beach! King Bed & Free Beach Passes
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
The price is HK$867
HK$1,942 total
includes taxes & fees
30 Nov - 1 Dec
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
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 HK$996
HK$2,152 total
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Property grounds
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Edgewater
The price is HK$16,801
HK$24,119 total
includes taxes & fees
30 Nov - 1 Dec
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
On the beach
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict
9.2 out of 10, Wonderful, (7)
"The owner was very nice "
United States
karen
The price is HK$1,400
HK$2,237 total
includes taxes & fees
10 Dec - 11 Dec
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Beach nearby, sun-loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 HK$958
HK$3,427 total
includes taxes & fees
2 Dec - 3 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is HK$1,120
HK$3,334 total
includes taxes & fees
30 Nov - 1 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
3 bedrooms, iron/ironing board, travel cot, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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 HK$1,400
HK$2,836 total
includes taxes & fees
1 Dec - 2 Dec
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Smart TV, fireplace, books, printers
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is HK$3,104
HK$6,884 total
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Interior
Upscale Condo in Annapolis

Upscale Condo in Annapolis

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 HK$2,225
HK$4,691 total
includes taxes & fees
15 Dec - 16 Dec
Upscale Condo in Annapolis
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 HK$1,331
HK$3,515 total
includes taxes & fees
1 Dec - 2 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
4 bedrooms, desk, iron/ironing board, travel cot
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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 HK$1,394
HK$3,595 total
includes taxes & fees
1 Dec - 2 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

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 HK$910
HK$2,403 total
includes taxes & fees
1 Dec - 2 Dec
Cozy 2br home w/ parking in downtown Annapolis
Beach
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick
10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
The price is HK$1,316
HK$2,740 total
includes taxes & fees
30 Nov - 1 Dec
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

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 HK$1,330
HK$4,294 total
includes taxes & fees
30 Nov - 1 Dec
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop
Fisher House: Steps From USNA + Covered Parking!

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 HK$2,024
HK$5,084 total
includes taxes & fees
1 Dec - 2 Dec
Fisher House: Steps From USNA + Covered Parking!
Beach
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Edgewater
10.0 out of 10, Exceptional, (2)
"Very comfortable home. We only stayed one night but the property was quiet and safe. Nice neighborhood to walk around, including a marina and small beach down the street."
United States
Jay B.
The price is HK$1,750
HK$2,793 total
includes taxes & fees
3 Dec - 4 Dec
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging

Annapolis
9.2 out of 10, Wonderful, (15)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
United States
Mike F.
The price is HK$1,376
HK$2,900 total
includes taxes & fees
10 Dec - 11 Dec
Wright's Cottage- Pet's Welcome & EV Charging
Interior
40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views

2.0 star property
Stevensville
40' Bristol sailboat with spectacular views
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

Country Inn & Suites by Radisson, Camp Springs (Andrews Air Force Base), MD

Country Inn & Suites by Radisson, Camp Springs (Andrews Air Force Base), MD

10/10 Excellent
"This was my second time coming within the period of two months. The service there is excellent. The beds are comfortable if something is wrong with the room or the exterior of the hotel it is taken care of expediently by management. I highly highly recommend this hotel. Dolly "
Dolly 6-night trip
Posted 16 hours ago
Country Inn & Suites by Radisson, Camp Springs (Andrews Air Force Base), MD

Find out more about Odyssey

Search for holiday rentals in Odyssey on Expedia! You can easily find your home rentals, villas, holiday apartments in Odyssey using one of the methods below:

  • View our selection of featured holiday rentals in Odyssey
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  • Enter your travel dates to view the best deals on holiday rentals in Odyssey while they last

Look no further and take a look at our great range of rental properties in Odyssey!

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.