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Odyssey Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Odyssey holiday rentals

Beach

1. 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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is HK$855
HK$2,839 total
includes taxes & fees
31 Aug - 1 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Outdoor dining

2. 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)
"Such a great house! "
United States
Stephanie V.
The price is HK$1,194
HK$3,758 total
includes taxes & fees
31 Aug - 1 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior detail

3. 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 HK$1,023
HK$2,614 total
includes taxes & fees
25 Aug - 26 Aug
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Terrace/patio

4. 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
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is HK$1,228
HK$2,830 total
includes taxes & fees
31 Aug - 1 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Interior

5. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is HK$2,140
HK$4,220 total
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!
Exterior

6. 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 HK$966
HK$2,543 total
includes taxes & fees
26 Aug - 27 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Property grounds

7. 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
9.2 out of 10, Wonderful, (15 reviews)
"The owner was very nice "
United States
karen
The price is HK$1,200
HK$2,103 total
includes taxes & fees
25 Aug - 26 Aug
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Pool

8. 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 HK$1,521
HK$4,060 total
includes taxes & fees
9 Sept - 10 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Living area

9. 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 HK$2,074
HK$4,492 total
includes taxes & fees
8 Sept - 9 Sept
3-bedroom house in Deale located on Bay many amenities and great views
Private kitchen

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 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 HK$1,639
HK$4,576 total
includes taxes & fees
27 Aug - 28 Aug
Renovated Bungalow | Walk to Beach | Dog-Friendly
Living area

11. 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 HK$1,898
HK$5,551 total
includes taxes & fees
25 Aug - 26 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
Exterior

12. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,136
HK$3,639 total
includes taxes & fees
25 Aug - 26 Aug
Plum Point Cottage #17
Marina

13. 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 HK$1,501
HK$4,000 total
includes taxes & fees
25 Aug - 26 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Dining

14. 4 Mi to Northwest Stadium: Inviting Home!

4 Mi to Northwest Stadium: Inviting Home!
Walker Mill
8.8 out of 10, Excellent, (12 reviews)
"We had a lovely stay"
United States
Charlese C.
The price is HK$1,184
HK$6,051 total
includes taxes & fees
25 Aug - 26 Aug
4 Mi to Northwest Stadium: Inviting Home!
Property grounds

15. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is HK$1,623
HK$2,809 total
includes taxes & fees
25 Aug - 26 Aug
Bright and airy waterfront getaway
Living area

16. 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 HK$1,898
HK$5,551 total
includes taxes & fees
25 Aug - 26 Aug
Londontowne Rancher | 3BR | Near Waterfront
Beach

17. 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 HK$1,898
HK$5,846 total
includes taxes & fees
25 Aug - 26 Aug
Londontowne Home | Beach | 3BR
Interior

18. 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 HK$1,560
HK$4,478 total
includes taxes & fees
15 Sept - 16 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
Marina

19. Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,688
HK$2,148 total
includes taxes & fees
28 Aug - 29 Aug
Sailboat Experience 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

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

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

8/10 Good
"The room was nice and clean. It is located in a very convenient area, with stores, restaurants, and gas stations right across the street. The complimentary breakfast was delicious, and the staff stayed on top of keeping the food fresh and in stock."
Jasmyn 2-night trip
Posted 4 hours ago
Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

Find out more about Odyssey

Search for holiday rentals in Odyssey on Expedia! You can easily find your home rentals, villas, holiday apartments in Odyssey using one of the methods below:

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Look no further and take a look at our great range of rental properties in Odyssey!

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 Breezy Point Beach. In the wider area, you’ll find Rod n Reel Charter Fishing and Chesapeake Beach Railway 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.