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Odyssey Holiday Rentals

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Our top choices for Odyssey holiday rentals

Admiral's Abode - Charming Retreat

Admiral's Abode - Charming Retreat
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Jessica J.
Admiral's Abode - Charming Retreat

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, (15 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is NZ$1,215
includes taxes & fees
14 July - 15 July
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 NZ$1,332
includes taxes & fees
22 June - 23 June
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is NZ$738
includes taxes & fees
8 July - 9 July
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

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)
"Clean and easy "
United States
Robert R.
The price is NZ$1,063
includes taxes & fees
5 July - 6 July
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is NZ$957
includes taxes & fees
23 June - 24 June
3-Bedroom Beach Home w/ Backyard

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 NZ$632
includes taxes & fees
30 June - 1 July
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$1,021
includes taxes & fees
22 June - 23 June
Sunset Cottage - West River Access and Views!

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (21 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is NZ$671
includes taxes & fees
24 June - 25 June
Walk to Beach! King Bed & Free Beach Passes

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.6 out of 10, Excellent, (4 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is NZ$1,010
includes taxes & fees
22 June - 23 June
Fabulous 5-bedroom house with AC in charming Annapolis

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 NZ$1,058
includes taxes & fees
14 July - 15 July
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is NZ$602
includes taxes & fees
24 June - 25 June
3-bedroom house in Deale located on Bay many amenities and great views

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The view was incredible! So magical. My daughters and I watched the sunrise over the bay every morning from the living room. On our last morning there was a family of deer grazing as we watched - it was so beautiful! The master bathroom is amazing. It was the perfect spot for family to gather for brunch before a wedding! "
United States
Lia D.
The price is NZ$1,368
includes taxes & fees
30 June - 1 July
Charming Annapolis WaterVIEW Home

5 bedroom house with EV charger Near Downtown Annapolis

5 bedroom house with EV charger Near Downtown Annapolis
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
United States
Jacob V.
5 bedroom house with EV charger Near Downtown Annapolis

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 NZ$1,184
includes taxes & fees
13 July - 14 July
Annapolis Retreat - 7 mins from downtown Annapolis!

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (7 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is NZ$1,039
includes taxes & fees
13 July - 14 July
Renovated Bungalow | Walk to Beach | Dog-Friendly

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is NZ$1,273
includes taxes & fees
20 June - 21 June
Secluded Cozy Cottage in Historic Downtown

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 NZ$1,178
includes taxes & fees
21 June - 22 June
Family Home on Mayo Peninsula | Deck | Sleeps 10

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
The price is NZ$1,636
includes taxes & fees
22 June - 23 June
Two Historic Rowhomes in Downtown Annapolis

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
The price is NZ$1,282
includes taxes & fees
21 June - 22 June
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
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

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, 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 NZ$497 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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Odyssey is located in the city centre, and has a fireplace, a patio 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Marlton Neighborhood Park. 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.