Odyssey Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Odyssey vacation rentals

Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (17)
"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 ￥12,596
￥50,642 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Walk to Beach! King Bed & Free Beach Passes
Marina
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

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 ￥335,902
￥488,056 total
includes taxes & fees
Dec 23 - Dec 24
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
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.

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 ￥17,845
￥40,016 total
includes taxes & fees
Dec 21 - Dec 22
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Exterior
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 ￥14,948
￥43,539 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Outdoor dining
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 ￥14,948
￥62,873 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior detail
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.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
North Beach
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is ￥19,905
￥43,023 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
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

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 ￥62,048
￥137,637 total
includes taxes & fees
Dec 21 - Dec 22
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Smart TV, fireplace, foosball, table tennis
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

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (8)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is ￥38,489
￥85,007 total
includes taxes & fees
Dec 22 - Dec 23
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Interior
Upscale Condo in Annapolis

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 ￥38,114
￥85,668 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Upscale Condo in Annapolis
Property grounds
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.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
The price is ￥27,992
￥46,538 total
includes taxes & fees
Dec 21 - Dec 22
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (7)
"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 ￥23,949
￥82,474 total
includes taxes & fees
Dec 22 - Dec 23
Cute bungalow blocks to Stadium
Smart TV
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

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 ￥26,872
￥72,118 total
includes taxes & fees
Dec 21 - Dec 22
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
TV, books, offices
Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is ￥24,882
￥84,918 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Holly Hill Haven - Sleeps 10
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!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
The price is ￥31,058
￥60,137 total
includes taxes & fees
Dec 21 - Dec 22
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Smart TV, books
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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, (5)
"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 ￥28,008
￥56,573 total
includes taxes & fees
Dec 21 - Dec 22
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Marina
Fisher House: Steps From USNA + Covered Parking!

Fisher House: Steps From USNA + Covered Parking!

Fisher House: Steps From USNA + Covered Parking!
Historic District
10.0 out of 10, Exceptional, (13)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is ￥49,948
￥119,735 total
includes taxes & fees
Dec 23 - Dec 24
Fisher House: Steps From USNA + Covered Parking!
Fridge, microwave, oven, stovetop
Golden Anchor Retreat; Lux Living! - Sleeps 7

Golden Anchor Retreat; Lux Living! - Sleeps 7

Golden Anchor Retreat; Lux Living! - Sleeps 7
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 ￥36,255
￥107,433 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Golden Anchor Retreat; Lux Living! - Sleeps 7
Interior
Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (4)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ￥26,296
￥82,483 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Annapolis Retreat - 7 mins from downtown Annapolis!
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 .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
10.0 out of 10, Exceptional, (4)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is ￥34,990
￥55,312 total
includes taxes & fees
Dec 20 - Dec 21
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Pool
Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is ￥27,230
￥69,097 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Family Beach House: Spacious Deck, Grill & 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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Awesone place to stay. Clean, comfortable, great location, courteous staff."
JAMES H COLMER 2-night trip
Posted 2 days ago
Historic Inns of Annapolis

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 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?

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!: This vacation home rental near Odyssey is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 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 garden and a selection of games.

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 Rod n Reel Charter Fishing and Chesapeake Beach Railway Museum.

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.