Odyssey Vacation Rentals from $269: Search Short-Term Rentals

Q: Can I find a vacation rental in Odyssey?

Yes, we give you a choice of vacation rentals near top local attractions in Odyssey, or you can select a more remote option if you're looking for a relaxing stay.

Q: What's the top vacation rental in Odyssey?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach : This vacation home rental near Odyssey is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

Q: 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 larger area, you’ll find Rod n Reel Charter Fishing and Chesapeake Beach Railway Museum.

Q: What are vacation rentals like in Odyssey?

Vacation rentals are privately owned accommodations you can book for several days or more in Odyssey. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.

Check prices for these dates

In two weeks

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Our top choices for Odyssey vacation rentals

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Ellen B.

$332 nightly

Aug 24 - Aug 25

Total with taxes and fees

2. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Stephanie V.

$440 nightly

Sep 8 - Sep 9

Total with taxes and fees

3. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

$257 nightly

Aug 17 - Aug 18

Total with taxes and fees

4. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

Joshua T.

$320 nightly

Aug 31 - Sep 1

Total with taxes and fees

5. Sunset Cottage - West River Access and Views!

Shady Side

Marci M.

$536 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

Edgewater

Kristin G.

$621 nightly

Aug 17 - Aug 18

Total with taxes and fees

7. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Bryan P.

$492 nightly

Sep 9 - Sep 10

Total with taxes and fees

8. Plum Point Cottage #17

Huntingtown

$421 nightly

Aug 17 - Aug 18

Total with taxes and fees

9. Modern Stay Hottub and Pool

Upper Marlboro

Diana H.

$766 nightly

Aug 19 - Aug 20

Total with taxes and fees

10. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

$654 nightly

Aug 17 - Aug 18

Total with taxes and fees

11. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

$447 nightly

Aug 17 - Aug 18

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Edgewater

Diane D.

$533 nightly

Sep 1 - Sep 2

Total with taxes and fees

13. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict

karen

$244 nightly

Aug 18 - Aug 19

Total with taxes and fees

14. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

"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."

Brian

$311 nightly

Aug 24 - Aug 25

Total with taxes and fees

15. Bright and airy waterfront getaway

Benedict

William N.

$353 nightly

Aug 24 - Aug 25

Total with taxes and fees

16. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"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. "

rebekah h.

$621 nightly

Aug 20 - Aug 21

Total with taxes and fees

Smart TV, fireplace, foosball, table tennis

17. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Homewood

Dan B.

$514 nightly

Aug 17 - Aug 18

Total with taxes and fees

18. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

$479 nightly

Aug 25 - Aug 26

Total with taxes and fees

19. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

$597 nightly

Sep 14 - Sep 15

Total with taxes and fees

20. Sailboat Experience in Annapolis

Parole

$269 nightly

Aug 18 - Aug 19

Total with taxes and fees

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Top Odyssey Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"It’s a wonderful place to rest nice and clean on point !! Highly recommended!!!"

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"This is our favorite hotel to stay in while in the Annapolis area. The hotel is clean inside and out. Staff are so wonderful and genuinely care about your happiness. And a price point that trumps other hotels by far. We've stayed at another hotel that is right beside this one and were very disappointed, but this hotel exceeds out expectations every time."

Rod 'N' Reel Resort

8/10 Good

"My son and I loved our stay. This is a wonderful resort with two pools, outdoor games, an awesome shower, and comfy beds. One downside, the restaurants on site do not deliver food to the rooms for room service. *Alpha Gal Syndrome note: there were about 4 restaurants on site, and it wasn’t for sure safe to order any hot well rounded meal due to beef and pork being cooked on the same grill. I didn’t call around, but information was shared by staff, so I chose not to risk it."

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

10/10 Excellent

"The Staff wasn’t knowledgeable about the Conference they was suppose to honor, The air conditioning system could have been cooler, The complimentary breakfast didn't accommodate people that don’t est pork, The room was very clean (personally my stay there was great and it was peaceful I would refer anyone there and I would go back"

Find out more about Odyssey

Everything you need to know about Odyssey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Odyssey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Odyssey vacation 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 low season months. For more hustle and bustle, you may prefer to visit Odyssey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $269 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Odyssey rentals

At Expedia, we put the best Odyssey vacation 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 vacation.

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 vacation rental in Odyssey?

Yes, we give you a choice of vacation rentals near top local attractions in Odyssey, or you can select a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Odyssey?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental near Odyssey is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Rod n Reel Charter Fishing and Chesapeake Beach Railway Museum.

What are vacation rentals like in Odyssey?

Vacation rentals are privately owned accommodations you can book for several days or more in Odyssey. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Odyssey vacation rentals

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

2. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

3. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

4. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

5. Sunset Cottage - West River Access and Views!

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

7. Family Beach House: Spacious Deck, Grill & Views

8. Plum Point Cottage #17

9. Modern Stay Hottub and Pool

10. Londontowne Home | Beach | 3BR

11. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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

13. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

14. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

15. Bright and airy waterfront getaway

16. Londontowne Rancher | 3BR | Near Waterfront

17. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

18. Annapolis Retreat - 7 mins from downtown Annapolis!

19. Charming Annapolis WaterVIEW Home

20. Sailboat Experience in Annapolis

Find vacation rentals that suit your style

Top Odyssey Hotel Reviews

Historic Inns of Annapolis

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

Rod 'N' Reel Resort

Comfort Inn Conference Center

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

Annapolis Waterfront Hotel, Autograph Collection

Country Inn & Suites by Radisson, Annapolis, MD

Comfort Inn Largo-Washington DC East

Find out more about Odyssey

Frequently asked questions

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