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Odyssey Holiday Rentals

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Our top choices for Odyssey holiday rentals

1. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is NZ$749
includes taxes & fees
21 Sept - 22 Sept
Rose Haven Coastal Cottage

2. 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, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is NZ$664
includes taxes & fees
28 Sept - 29 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away

3. 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, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is NZ$740
includes taxes & fees
23 Sept - 24 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

4. 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$874
includes taxes & fees
30 Sept - 1 Oct
3-bedroom house in Deale located on Bay many amenities and great views

5. 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.
The price is NZ$596
includes taxes & fees
8 Oct - 9 Oct
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

6. 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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is NZ$694
includes taxes & fees
30 Sept - 1 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

7. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 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 NZ$974
includes taxes & fees
6 Oct - 7 Oct
Sunset Cottage - West River Access and Views!

8. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is NZ$802
includes taxes & fees
18 Sept - 19 Sept
Plum Point Cottage #17

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is NZ$1,211
includes taxes & fees
20 Sept - 21 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10

10. 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$791
includes taxes & fees
20 Sept - 21 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

11. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is NZ$505
includes taxes & fees
20 Sept - 21 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

12. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 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.
The price is NZ$1,324
includes taxes & fees
18 Sept - 19 Sept
Londontowne Home | Beach | 3BR

13. 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, (19 reviews)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is NZ$802
includes taxes & fees
21 Sept - 22 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

14. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"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. "
United States
rebekah h.
The price is NZ$1,211
includes taxes & fees
20 Sept - 21 Sept
Londontowne Rancher | 3BR | Near Waterfront

15. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is NZ$1,106
includes taxes & fees
21 Sept - 22 Sept
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is NZ$1,084
includes taxes & fees
4 Oct - 5 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly

17. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"Overall I had a wonderful stay... however I wish it was booked for a summertime day... the brand new pool looked very appealing & I wish I couldve enjoyed using it. Will have to try & stay again during the summer for a nice pool day!"
United States
Jay W.
The price is NZ$1,306
includes taxes & fees
21 Sept - 22 Sept
Tranquil Modern Farmhouse

18. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
7.6 out of 10, Good, (4 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is NZ$1,841
includes taxes & fees
20 Sept - 21 Sept
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

19. Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME

Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME
Waldorf
The price is NZ$1,069
includes taxes & fees
1 Oct - 2 Oct
Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME

20. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is NZ$783
includes taxes & fees
22 Sept - 23 Sept
The Harness Creek Retreat in Annapolis
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$505 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 Shadyside Park. In the wider area, you’ll find Rod n Reel Charter Fishing and Show Place Arena.

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.