Odyssey Holiday Rentals from €261: Search Short-Term Rentals

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Holiday Rentals in Odyssey

"The views are fantastic. Very quiet neighborhood. "

"Loved the location and the pristine condition of the house. "

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."

"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "

"Excellent location, Excellent property, Excellent owners!"

"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"

"Easy checkin/checkout. Cute cottage. Scenic and comfortable."

"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"

"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "

includes taxes & fees

27 Aug - 28 Aug

"Modern, Fresh, Clean! No complaints at all!"

"Just perfect for a 4 night stay."

"This exceptional property was our best homestay experience yet across several states and countries. The unit has so many customized features that make it stand out, from the fire pit (fire already built) and sauna (water bucket already filled) to the kitchen and bedrooms, where no detail has been missed. The owners were extremely proactive and responsive throughout our stay, and we look forward to booking again soon. "

"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"

includes taxes & fees

9 Sept - 10 Sept

"Clean, quiet, and very close to both downtown and Eastport restaurants."

"Excellent property, great communication with the hosts. Quite and relaxing"

"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "

includes taxes & fees

27 Aug - 28 Aug

"Great location, comfortable stay!!"

"Great location, great host! "

includes taxes & fees

3 Sept - 4 Sept

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Top Odyssey Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"Friendly and accommodating staff! Room was bright, comfortable, cozy, and clean! Nice amenities like a small fridge and single cup coffee maker in the room. Be careful stepping into the shower, as it's a little slippery. Perhaps some "non-skid" strips or a mat of some sort on the bottom of the tub. Overall, great stay! Highly recommend! "

Hampton Inn & Suites Annapolis

10/10 Excellent

"It's poorly maintained. Baseboard in room coming off corner into the bathroom. Paint peeling off the bathroom door. Bathroom faucet was loose. The toilet seat was loose. Toilet runs on and off all the time. It was a very dark room, low wattage light bulbs and one of the lamps didn't work. There's a leak somewhere from the tub even when the shower curtain is closed and leaves a puddle. The Staff was very friendly though the lobby was old and dirty. We were supposed to stay there 6 days but left after the first night."

Courtyard by Marriott Annapolis

10/10 Excellent

"The staff was very friendly, our room and surrounding areas (hallway, courtyard, parking lot) were very clean. But somehow water would leak out of the shower and make a puddle on the floor. The carpet outside the tile in front of the closet would also get wet. We couldn't figure out how."

Find out more about Odyssey

Everything you need to know about Odyssey holiday rentals

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

Odyssey holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Odyssey holiday rentals we have selected for you start as low as €261 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 holiday 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 holiday.

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 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?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of Odyssey is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area, you’ll find Fridays Creek Winery and Bayside History 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.

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Holiday Rentals in Odyssey

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Holiday Rentals in Odyssey

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

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Bay views with kayaks, bikes, fire pit, crabbing and more

Floating 2 bed 2 bath condo stunning views of the bay

Private Cottage on gated estate

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

The Yellow Cottage on Harness Creek

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Waterfront Getaway, Dock Your Boat & Play!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Chesapeake Houseboat Getaway on Kent Island, Maryland

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

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Beautiful Condo - Water View Near City Dock

25-50% Off~Private Beach~Hot Tub~Fire Table~

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

Annapolis Home Near Beach & Quiet Waters Park!

USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!

Top Odyssey Hotel Reviews

Historic Inns of Annapolis

Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

SpringHill Suites by Marriott Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Hampton Inn & Suites Annapolis

Courtyard by Marriott Annapolis

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Comfort Inn Conference Center

Graduate by Hilton Annapolis

Find out more about Odyssey

Frequently asked questions