Default HTG hotel image

Odyssey Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Odyssey vacation rentals

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $396
CA $892 total
includes taxes & fees
Jun 30 - Jul 1
Family Beach House: Spacious Deck, Grill & Views

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, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is CA $200
CA $491 total
includes taxes & fees
Jul 1 - Jul 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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
9.6 out of 10, Exceptional, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $505
CA $981 total
includes taxes & fees
Jul 13 - Jul 14
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community 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, (12 reviews)
"Listing was accurate; communication with host was great and helpful. We had a wonderful family time."
United States
Melissa D.
The price is CA $522
CA $891 total
includes taxes & fees
Jul 5 - Jul 6
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Annapolis Garden Suite

Annapolis Garden Suite
Epping Forest
10.0 out of 10, Exceptional, (17 reviews)
"We had a quick overnight stay to attend an event at the Naval Academy! This was the perfect spot!! The accommodations were exactly what we needed!! Thanks for a great stay!!! "
United States
Mary S.
The price is CA $360
CA $689 total
includes taxes & fees
Jul 7 - Jul 8
Annapolis Garden Suite

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $387
CA $653 total
includes taxes & fees
Jul 1 - Jul 2
Plum Point Cottage #17

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is CA $452
CA $590 total
includes taxes & fees
Jul 15 - Jul 16
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.4 out of 10, Very good, (5 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is CA $565
CA $828 total
includes taxes & fees
Jun 30 - Jul 1
Fabulous 5-bedroom house with AC in charming Annapolis

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

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is CA $524
CA $1,007 total
includes taxes & fees
Jun 30 - Jul 1
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (71 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is CA $511
CA $1,015 total
includes taxes & fees
Jun 30 - Jul 1
Charming Annapolis WaterVIEW Home

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (8 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is CA $383
CA $937 total
includes taxes & fees
Jul 16 - Jul 17
Renovated Bungalow | Walk to Beach | Dog-Friendly

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $344
CA $984 total
includes taxes & fees
Jun 30 - Jul 1
Family Home on Mayo Peninsula | Deck | Sleeps 10

Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
The price is CA $344
CA $984 total
includes taxes & fees
Jun 30 - Jul 1
Londontowne Rancher | 3BR | Near Waterfront

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is CA $639
CA $1,063 total
includes taxes & fees
Jul 1 - Jul 2
Secluded Cozy Cottage in Historic Downtown

Franklin At The Bay

Franklin At The Bay
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
The price is CA $497
CA $921 total
includes taxes & fees
Jul 7 - Jul 8
Franklin At The Bay

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home for a girls weekend away. The view is spectacular, host was communicative, and lots of thoughtful small touches throughout the home and the experience. Thank you for a wonderful stay! "
United States
Katie K.
The price is CA $456
CA $844 total
includes taxes & fees
Jul 6 - Jul 7
Sunset Cottage - West River Access and Views!

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is CA $355
CA $906 total
includes taxes & fees
Jul 13 - Jul 14
Annapolis Retreat - 7 mins from downtown Annapolis!

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (82 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is CA $422
CA $772 total
includes taxes & fees
Jul 1 - Jul 2
Cozy 2br home w/ parking in downtown Annapolis

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is CA $226
CA $603 total
includes taxes & fees
Jul 15 - Jul 16
Walk to Beach! King Bed & Free Beach Passes

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, (9 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is CA $217
CA $382 total
includes taxes & fees
Jun 30 - Jul 1
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Odyssey Hotel Reviews

Find out more about Odyssey

Everything you need to know about Odyssey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Odyssey vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Odyssey vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Odyssey vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Odyssey vacation rentals we have selected for you start as low as CA $382 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Odyssey rentals

At Expedia, we put the best Odyssey vacation 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 vacation.

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 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?

Charming Annapolis WaterVIEW Home: This vacation home rental near Odyssey is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 selection of games and a hot tub.

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 Bayside History Museum and Rod n Reel Charter Fishing.

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.