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Odyssey Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is HK$755
HK$2,635 total
includes taxes & fees
21 Oct - 22 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

2. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"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 HK$1,766
HK$3,391 total
includes taxes & fees
14 Oct - 15 Oct
Rose Haven Coastal Cottage
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is HK$934
HK$2,246 total
includes taxes & fees
15 Oct - 16 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

4. 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, (39 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 HK$1,159
HK$3,583 total
includes taxes & fees
3 Nov - 4 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

5. 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$1,413
HK$3,426 total
includes taxes & fees
18 Oct - 19 Oct
3-bedroom house in Deale located on Bay many amenities and great views
A deck with outdoor furniture, a red door, and a house with windows.

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 HK$1,349
HK$2,969 total
includes taxes & fees
26 Oct - 27 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

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 HK$1,774
HK$3,766 total
includes taxes & fees
10 Nov - 11 Nov
Sunset Cottage - West River Access and Views!
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$1,130
HK$3,570 total
includes taxes & fees
27 Oct - 28 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Three Adirondack chairs facing a beach with a clear view of the ocean.

9. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is HK$2,566
HK$4,246 total
includes taxes & fees
14 Oct - 15 Oct
Plum Point Cottage #14
An outdoor dining area with a wooden table and chairs, a bottle of wine, and a vase of flowers.

10. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is HK$2,558
HK$4,480 total
includes taxes & fees
14 Oct - 15 Oct
Plum Point Cottage #15
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$2,072
HK$5,779 total
includes taxes & fees
21 Oct - 22 Oct
Family Home on Mayo Peninsula | Deck | Sleeps 10
A single-story house with a front porch, a mailbox, and an American flag.

12. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,138
HK$3,592 total
includes taxes & fees
14 Oct - 15 Oct
Plum Point Cottage #17
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

13. 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 HK$1,640
HK$4,554 total
includes taxes & fees
20 Oct - 21 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

14. 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)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is HK$1,201
HK$2,105 total
includes taxes & fees
14 Oct - 15 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

15. 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)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is HK$791
HK$2,384 total
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

16. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is HK$2,246
HK$3,382 total
includes taxes & fees
5 Nov - 6 Nov
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A beach with chairs and a pier in the background.

17. 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)
The price is HK$1,483
HK$3,704 total
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

18. 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 HK$3,305
HK$6,068 total
includes taxes & fees
19 Oct - 20 Oct
Tranquil Modern Farmhouse
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

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$2,069
HK$5,777 total
includes taxes & fees
14 Oct - 15 Oct
Londontowne Rancher | 3BR | Near Waterfront
A calm lake with a sandy shore, surrounded by trees and houses.

20. 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$2,260
HK$6,316 total
includes taxes & fees
18 Oct - 19 Oct
Londontowne Home | Beach | 3BR
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Clean room. Great breakfast."
Eric 2-night trip
Posted less than an hour ago
Crowne Plaza Annapolis 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:

  • View our selection of featured holiday rentals in Odyssey
  • Use the map to find apartments and other holiday homes in the Odyssey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Odyssey while they last

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 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.