Odyssey Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Odyssey holiday rentals

Interior
Upscale Condo in Annapolis

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (2 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is HK$1,465
HK$3,741 total
includes taxes & fees
22 Jan - 23 Jan
Upscale Condo in Annapolis
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (17 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is HK$549
HK$2,414 total
includes taxes & fees
14 Jan - 15 Jan
Walk to Beach! King Bed & Free Beach Passes
Exterior detail
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is HK$1,122
HK$2,305 total
includes taxes & fees
14 Jan - 15 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Dining
Haven 2

Holiday Home in Waldorf

Haven 2
2.5 star property
The price is HK$347
HK$776 total
includes taxes & fees
16 Jan - 17 Jan
Haven 2
Outdoor dining
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Holiday Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$909
HK$3,345 total
includes taxes & fees
21 Jan - 22 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is HK$547
HK$1,943 total
includes taxes & fees
14 Jan - 15 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Smart TV, fireplace, books, printers
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is HK$3,110
HK$6,891 total
includes taxes & fees
22 Jan - 23 Jan
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Smart TV
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Holiday Home in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is HK$1,235
HK$3,488 total
includes taxes & fees
14 Jan - 15 Jan
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Beach
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Holiday Home in Edgewater

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is HK$1,754
HK$2,781 total
includes taxes & fees
14 Jan - 15 Jan
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Cottage in Owings

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (48 reviews)
"We love this place!"
United States
Joan K.
The price is HK$1,100
HK$2,249 total
includes taxes & fees
15 Jan - 16 Jan
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
TV, books, offices
Holly Hill Haven - Sleeps 10

Holiday Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,122
HK$4,310 total
includes taxes & fees
3 Feb - 4 Feb
Holly Hill Haven - Sleeps 10
Interior
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Holiday Home in Historic District

Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is HK$1,239
HK$5,767 total
includes taxes & fees
14 Jan - 15 Jan
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Marina
Secluded Cozy Cottage in Historic Downtown

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16 reviews)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
The price is HK$1,929
HK$3,763 total
includes taxes & fees
14 Jan - 15 Jan
Secluded Cozy Cottage in Historic Downtown
Property grounds
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cottage in Benedict

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.0 out of 10, Wonderful, (8 reviews)
"The owner was very nice "
United States
karen
The price is HK$1,403
HK$2,242 total
includes taxes & fees
16 Jan - 17 Jan
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Fridge, microwave, oven, stovetop
Stunning 4 BR Home - Walking Distance to Stadium

Holiday Home in Homewood

Stunning 4 BR Home - Walking Distance to Stadium
10.0 out of 10, Exceptional, (2 reviews)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
Stunning 4 BR Home - Walking Distance to Stadium
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is HK$1,930
HK$3,781 total
includes taxes & fees
26 Jan - 27 Jan
Annapolis Gem: Stylish and Cozy
Fridge, microwave, oven, stovetop
Golden Anchor Retreat; Lux Living! - Sleeps 7

Holiday Home in Edgewater

Golden Anchor Retreat; Lux Living! - Sleeps 7
10.0 out of 10, Exceptional, (2 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$1,551
HK$5,021 total
includes taxes & fees
14 Jan - 15 Jan
Golden Anchor Retreat; Lux Living! - Sleeps 7
Fridge, microwave, oven, stovetop
All Star Annapolis Retreat - Walk to Stadium

Holiday Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Great house, perfect for Navy football game"
United States
Kathy N.
The price is HK$1,949
HK$6,336 total
includes taxes & fees
14 Jan - 15 Jan
All Star Annapolis Retreat - Walk to Stadium
Interior
Annapolis Retreat - 7 mins from downtown Annapolis!

Holiday Home in Hillsmere

Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,317
HK$4,159 total
includes taxes & fees
26 Jan - 27 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
Microwave, oven, stovetop, dishwasher
Fabulous 5-bedroom house with AC in charming Annapolis

Holiday Home in Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is HK$2,988
HK$4,402 total
includes taxes & fees
26 Jan - 27 Jan
Fabulous 5-bedroom house with AC in charming 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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"H"
William 2-night trip
Posted 5 days ago
Historic Inns of Annapolis

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?

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This holiday home rental outside of Odyssey is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 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.