Odyssey Vacation Rentals

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Check prices for these dates

Tonight
Dec 19 - Dec 20
Tomorrow
Dec 20 - Dec 21
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Odyssey vacation rentals

Interior
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Historic District
10.0 out of 10, Exceptional, (33)
"Beautiful home in a great central location for walking to most downtown and USNA destinations. "
United States
Hunter S.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Interior
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
Stevensville
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Property grounds
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Admiral Heights
10.0 out of 10, Exceptional, (89)
"Fantastic stay the house was perfect."
United States
Eric Z.
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Exterior
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.4 out of 10, Exceptional, (20)
"Great place, excellent location!"
United States
Joseph C.
The price is ￥100,211
￥183,202 total
includes taxes & fees
Dec 20 - Dec 21
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Fridge, microwave, oven, stovetop
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Historic District
9.8 out of 10, Exceptional, (30)
"Pet friendly! Super cute and easy…perfect location. "
United States
Jennifer B.
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Interior
Annapolis Condominium in the heart of the historic center

Annapolis Condominium in the heart of the historic center

Annapolis Condominium in the heart of the historic center
Historic District
9.8 out of 10, Exceptional, (293)
"Great stay! Easy check in, great location."
United States
Erin W.
Annapolis Condominium in the heart of the historic center
Interior
Romantic Two Bedroom Condo

Romantic Two Bedroom Condo

Romantic Two Bedroom Condo
Crofton
9.8 out of 10, Exceptional, (94)
"After moving to North Carolina last month We had a great visit with our family who were only a few houses away! My grandson was thrilled and family is what it’s about The host was extra accommodating for us. "
United States
Valerie H.
Romantic Two Bedroom Condo
Smart TV
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Crofton
9.8 out of 10, Exceptional, (101)
"Lovely place, family friendly, clean and wonderful host. Location was also a plus with a close proximity to restaurants and shops and only 20 min from Annapolis.We would definitely stay here again!"
United States
Brenda R.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Terrace/patio
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Port Republic
10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!
Edgewater
10.0 out of 10, Exceptional, (3)
"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.
Waterfront Getaway, Dock Your Boat & Play!
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater
9.8 out of 10, Exceptional, (25)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is ￥34,854
￥101,499 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Edgewater/Mayo Gateaway w/ Hot Tub
Dining
Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay
Deale
9.8 out of 10, Exceptional, (131)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of the Chesapeake Bay
Exterior
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Stevensville
10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Exterior
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Cape St. John
10.0 out of 10, Exceptional, (114)
"We had a wonderful stay. The house was beautiful, clean, fully equipped and the views out back are magnificent. We all loved the pool. The host was very helpful with any issues & requests. All in all we truly enjoyed our time there. Highly recommend."
United States
Zev K.
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Marina
Beautiful Condo - Water View Near City Dock

Beautiful Condo - Water View Near City Dock

Beautiful Condo - Water View Near City Dock
Eastport
9.6 out of 10, Exceptional, (155)
"Exceptionally clean property in a great location, convenient to DTA and the Naval Academy. The host was responsive and helpful throughout our stay. We would definitely stay here again!"
United States
Stephanie S.
Beautiful Condo - Water View Near City Dock
Smart TV, DVD player, books
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek
Hillsmere
10.0 out of 10, Exceptional, (170)
"Love the decor, the comfort and vibe of the place. Wish I had stayed longer! "
United States
Lauren m.
The Yellow Cottage on Harness Creek
Beach nearby, sun loungers, beach towels
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes
North Beach
10.0 out of 10, Exceptional, (76)
"Wonderful cottage within walking distance to fun dining experiences, the beach, and the pier as well as some cute shops. Very well appointed--comfortable and clean. We enjoyed our stay and would highly recommend this cottage!"
United States
Nancy K.
The Blue Crab Beach House - Free beach passes
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 .
Exterior
PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history
Historic District
10.0 out of 10, Exceptional, (214)
"Perfect location! Ample room for our family of five.. can’t wait to return. "
United States
Christine A.
PERFECT LOCATION in the heart of history
Dining
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views
Tilghman Island
9.8 out of 10, Exceptional, (10)
"Great property!!! Absolutely would recommend!"
United States
John and Michele E.
Bayfront Retreat Near St. Michaels | Private Dock • Sunset 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:

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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 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.