Odyssey Holiday Rentals from €231: Search Short-Term Rentals

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Our top choices for Odyssey holiday rentals

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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

North Beach

Johanna S.

includes taxes & fees

28 Oct - 29 Oct

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

North Beach

James L.

includes taxes & fees

19 Oct - 20 Oct

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Sarah

includes taxes & fees

9 Nov - 10 Nov

A house with a yellow door and a window with a lamp outside.

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

Deale

Maude H.

includes taxes & fees

15 Nov - 16 Nov

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

Anthony P.

includes taxes & fees

19 Oct - 20 Oct

A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

6. Rose Haven Coastal Cottage

North Beach

Sodbileg

includes taxes & fees

19 Oct - 20 Oct

A deck with outdoor furniture, a red door, and a house with windows.

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

David S.

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

8. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

9. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

includes taxes & fees

10 Nov - 11 Nov

10. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Chesapeak beach

Bryan P.

includes taxes & fees

27 Oct - 28 Oct

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

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

Benedict

ed r.

includes taxes & fees

19 Oct - 20 Oct

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

12. Renovated Bungalow | Walk to Beach | Dog-Friendly

Edgewater

Diane D.

includes taxes & fees

19 Oct - 20 Oct

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

13. Family Home on Mayo Peninsula | Deck | Sleeps 10

Edgewater

Kristin G.

includes taxes & fees

21 Oct - 22 Oct

A single-story house with a front porch, a mailbox, and an American flag.

14. Plum Point Cottage #17

Huntingtown

includes taxes & fees

19 Oct - 20 Oct

Three Adirondack chairs facing a beach with a clear view of the ocean.

15. Plum Point Cottage #14

Huntingtown

Yonnick H.

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

16. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

3 Nov - 4 Nov

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

17. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

A bedroom with a bed, a sofa, a wooden coffee table, and a ceiling fan.

18. Plum Point Cottage #15

Maryland

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

19. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"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. "

rebekah h.

includes taxes & fees

19 Oct - 20 Oct

A beach with chairs and a pier in the background.

20. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Pamela B.

includes taxes & fees

3 Nov - 4 Nov

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Top Odyssey Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"Extremely spacious, nicely appointed room."

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 €231 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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Odyssey is located near the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games 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 Jug Bay Wetlands Sanctuary. In the wider area, you’ll find Bayside History Museum and Rod n Reel Charter Fishing.

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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Check prices for these dates

Our top choices for Odyssey holiday rentals

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

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

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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