Odyssey Vacation Rentals

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Our top choices for Odyssey vacation rentals

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, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is CA $95
CA $344 total
includes taxes & fees
Apr 19 - Apr 20
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is CA $137
CA $479 total
includes taxes & fees
Apr 19 - Apr 20
Walk to Beach! King Bed & Free Beach Passes

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
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is CA $289
CA $598 total
includes taxes & fees
Apr 20 - Apr 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $234
CA $610 total
includes taxes & fees
Apr 20 - Apr 21
Family Beach House: Spacious Deck, Grill & Views

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 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 $211
CA $366 total
includes taxes & fees
Apr 17 - Apr 18
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $237
CA $668 total
includes taxes & fees
Apr 21 - Apr 22
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is CA $374
CA $700 total
includes taxes & fees
Apr 20 - Apr 21
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is CA $413
CA $598 total
includes taxes & fees
Apr 16 - Apr 17
40' Bristol sailboat with spectacular views

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, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is CA $384
CA $811 total
includes taxes & fees
Apr 28 - Apr 29
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is CA $180
CA $621 total
includes taxes & fees
Apr 28 - Apr 29
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is CA $209
CA $805 total
includes taxes & fees
Apr 21 - Apr 22
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"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.
The price is CA $140
CA $479 total
includes taxes & fees
Apr 16 - Apr 17
Waterfront Unit | Dock, Kayaks & SUPs Included

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.2 out of 10, Wonderful, (5 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is CA $189
CA $670 total
includes taxes & fees
Apr 16 - Apr 17
Renovated Bungalow | Walk to Beach | Dog-Friendly

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 $246
CA $749 total
includes taxes & fees
Apr 27 - Apr 28
Annapolis Retreat - 7 mins from downtown Annapolis!

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (2 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $302
CA $656 total
includes taxes & fees
Apr 21 - Apr 22
Sunset Cottage - West River Access and Views!

Historic Annapolis Home | 2 Blocks to Main St

Historic Annapolis Home | 2 Blocks to Main St
Historic District
10.0 out of 10, Exceptional, (16 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is CA $315
CA $954 total
includes taxes & fees
Apr 19 - Apr 20
Historic Annapolis Home | 2 Blocks to Main St

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
The price is CA $305
CA $846 total
includes taxes & fees
Apr 26 - Apr 27
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is CA $204
CA $482 total
includes taxes & fees
May 5 - May 6
Cozy 2br home w/ parking in downtown Annapolis

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is CA $295
CA $746 total
includes taxes & fees
May 4 - May 5
Cute bungalow blocks to Stadium

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is CA $275
CA $995 total
includes taxes & fees
Apr 21 - Apr 22
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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

Find out more about Odyssey

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Odyssey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Sweet Bamboo Beach Cottage: This vacation home rental near Odyssey is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so 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 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.