Default HTG hotel image

Odyssey Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Odyssey vacation rentals

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.
Benedict
9.2 out of 10, Wonderful, (10 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.
$241 nightly
The price is $266
Jul 15 - Jul 16
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

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, (47 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
$269 nightly
The price is $290
Jul 12 - Jul 13
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
$349 nightly
The price is $369
Jul 15 - Jul 16
Total with taxes and fees
Bright and airy waterfront getaway
Exterior detail

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
$268 nightly
The price is $305
Jul 14 - Jul 15
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Terrace/patio

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
$252 nightly
The price is $288
Jul 19 - Jul 20
Total with taxes and fees
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Fridge, microwave, oven, stovetop

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.
$542 nightly
The price is $618
Jul 16 - Jul 17
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-Friendly
Beach nearby

Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
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.
$351 nightly
The price is $387
Jul 12 - Jul 13
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away
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, (52 reviews)
"We love this place!"
United States
Joan K.
$387 nightly
The price is $410
Jul 28 - Jul 29
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
$269 nightly
The price is $274
Jul 10 - Jul 11
Total with taxes and fees
Sailboat Experience in Annapolis
Fridge, microwave, oven, stovetop

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
$344 nightly
The price is $392
Jul 12 - Jul 13
Total with taxes and fees
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
TV, offices

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$608 nightly
The price is $693
Jul 13 - Jul 14
Total with taxes and fees
Family Home on Mayo Peninsula | Deck | Sleeps 10
Beach

Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
10.0 out of 10, Exceptional, (2 reviews)
"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.
$648 nightly
The price is $739
Jul 12 - Jul 13
Total with taxes and fees
Londontowne Home | Beach | 3BR
Interior

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.
$639 nightly
The price is $650
Aug 3 - Aug 4
Total with taxes and fees
Sunset Cottage - West River Access and Views!
Exterior

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
$415 nightly
The price is $458
Jul 10 - Jul 11
Total with taxes and fees
Plum Point Cottage #17
Smart TV, fireplace, foosball, table tennis

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.
$558 nightly
The price is $636
Jul 13 - Jul 14
Total with taxes and fees
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Beach nearby, sun loungers, beach towels

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.
$607 nightly
The price is $691
Jul 13 - Jul 14
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Interior

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.
$555 nightly
The price is $633
Jul 22 - Jul 23
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
Pool

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.
$589 nightly
The price is $624
Jul 14 - Jul 15
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Smart TV, fireplace, computer monitors, printers

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"The host communicated immediately if needed. The house has practically everything a family needs. Fully stocked kitchen for meal prep, wonderful towels and memory foam beds. A wonderful rental."
United States
Kymme
$685 nightly
The price is $756
Jul 12 - Jul 13
Total with taxes and fees
Tranquil Modern Farmhouse
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
$465 nightly
The price is $527
Jul 22 - Jul 23
Total with taxes and fees
Cute bungalow blocks to Stadium
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Odyssey Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The pool time for both pools is 8am-8pm which seems ridiculous during the summer. Also advertising a beach, but there isn’t any access to the water to swim. Other than that we had a great time. The staff is excellent!!!!"
Terri 2-night trip
Posted 4 hours ago
Rod 'N' Reel Resort

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Odyssey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $266 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 Merkle Wildlife Sanctuary. 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.