Odyssey Holiday Rentals

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Check prices for these dates

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Odyssey

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

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 HK$613
HK$2,026 total
includes taxes & fees
2 Dec - 3 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

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 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.

Cottage in Owings

10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
The price is HK$866
HK$1,940 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.

Cottage in North Beach

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
The price is HK$996
HK$2,152 total
includes taxes & fees
30 Nov - 1 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.

Houseboat in Edgewater

The price is HK$16,800
HK$24,161 total
includes taxes & fees
29 Nov - 30 Nov
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.

Cottage in Benedict

9.2 out of 10, Wonderful, (7)
"The owner was very nice "
United States
karen
The price is HK$1,400
HK$2,328 total
includes taxes & fees
29 Nov - 30 Nov
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

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 HK$1,109
HK$3,620 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

Holiday Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is HK$1,120
HK$3,316 total
includes taxes & fees
29 Nov - 30 Nov
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.

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 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

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 HK$3,103
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

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 HK$2,224
HK$4,726 total
includes taxes & fees
4 Dec - 5 Dec
Upscale Condo in Annapolis
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 HK$1,435
HK$3,649 total
includes taxes & fees
9 Dec - 10 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

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 HK$1,400
HK$3,600 total
includes taxes & fees
9 Dec - 10 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina
Cozy 2br home w/ parking in downtown Annapolis

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 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!

Holiday Home in Prince Frederick

10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
The price is HK$1,594
HK$3,067 total
includes taxes & fees
1 Dec - 2 Dec
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

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 HK$1,330
HK$4,293 total
includes taxes & fees
30 Nov - 1 Dec
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop
Fisher House: Steps From USNA + Covered Parking!

Holiday Home in Historic District

10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
The price is HK$1,906
HK$4,929 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 .

Holiday Home in 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

Holiday Home in Annapolis

9.2 out of 10, Wonderful, (15)
"The property was well cleaned and communication with owner was excellent. Would stay again"
United States
Kristen
The price is HK$1,374
HK$2,897 total
includes taxes & fees
10 Dec - 11 Dec
Wright's Cottage- Pet's Welcome & EV Charging
Interior
40' Bristol sailboat with spectacular views

Houseboat in Stevensville

2.0 star property
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

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"All of the above!!"
Randolph 1-night trip
Posted 9 hours ago
Comfort Inn Conference Center

Find out more about Odyssey

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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.