Vacation rentals in Odyssey, MD

41 available vacation rental offers

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Best vacation rentals and Airbnb offers in Odyssey, MD

1 Mi to Boardwalk: Convenient North Beach Apt! - Odyssey, MD

1 Mi to Boardwalk: Convenient North Beach Apt!

Apartment, Odyssey

1 Mi to Boardwalk: Convenient North Beach Apt! is a apartment in Odyssey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About 1 Mi to Boardwalk: Convenient North Beach Apt!

1 Mi to Boardwalk: Convenient North Beach Apt! is a apartment in Odyssey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,238.

From$146/night
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Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Odyssey, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Odyssey

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Odyssey, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Odyssey, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,684.

From$150/night
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1 Mi to Boardwalk: Convenient North Beach Apt! - Odyssey, MD

1 Mi to Boardwalk: Convenient North Beach Apt!

Apartment, Odyssey

1 Mi to Boardwalk: Convenient North Beach Apt! is a apartment in Odyssey, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About 1 Mi to Boardwalk: Convenient North Beach Apt!

1 Mi to Boardwalk: Convenient North Beach Apt! is a apartment in Odyssey, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,102.

From$157/night
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Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis - Odyssey, MD

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

Apartment, Odyssey

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Odyssey, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About 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 is a apartment in Odyssey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,155.

From$165/night
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Vacation rentals with a pool in Odyssey, MD

Add a pool to the search when you want an easy place to cool off between outings.

42 Acres of Serenity & Nature Just 15 Miles To Annapolis - Odyssey, MD

42 Acres of Serenity & Nature Just 15 Miles To Annapolis

Holiday Home, Odyssey

42 Acres of Serenity & Nature Just 15 Miles To Annapolis is a holiday home in Odyssey, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 42 Acres of Serenity & Nature Just 15 Miles To Annapolis

42 Acres of Serenity & Nature Just 15 Miles To Annapolis is a holiday home in Odyssey, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,917.

From$988/night
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Private Pool Paradise Modest Socials Welcomed - Odyssey, MD

Private Pool Paradise Modest Socials Welcomed

Holiday Home, Odyssey

Private Pool Paradise Modest Socials Welcomed is a holiday home in Odyssey, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Private Pool Paradise Modest Socials Welcomed

Private Pool Paradise Modest Socials Welcomed is a holiday home in Odyssey, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,450.

From$1,493/night
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The Inn at Tacaro Estate - Odyssey, MD

The Inn at Tacaro Estate

B & B, Odyssey

The Inn at Tacaro Estate is a b & b in Odyssey, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About The Inn at Tacaro Estate

The Inn at Tacaro Estate is a b & b in Odyssey, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,583.

From$449/night
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Vacation rentals with parking in Odyssey, MD

Find vacation rentals that make arriving by car easier.

The Haven at Mariama House - Odyssey, MD

The Haven at Mariama House

Homestay, Odyssey

The Haven at Mariama House is a homestay in Odyssey, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About The Haven at Mariama House

The Haven at Mariama House is a homestay in Odyssey, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $442.

From$52/night
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Mission-Ready Retreat 18 Mi to Andrews AFB! - Odyssey, MD

Mission-Ready Retreat 18 Mi to Andrews AFB!

Holiday Home, Odyssey

Mission-Ready Retreat 18 Mi to Andrews AFB! is a holiday home in Odyssey, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Mission-Ready Retreat 18 Mi to Andrews AFB!

Mission-Ready Retreat 18 Mi to Andrews AFB! is a holiday home in Odyssey, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,332.

From$190/night
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Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. - Odyssey, MD

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.

Guest House, Odyssey

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. is a guest house in Odyssey, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. is a guest house in Odyssey, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,617.

From$231/night
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Rose Haven Peaceful, Spacious, 3 Bedroom Retreat - Odyssey, MD

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Holiday Home, Odyssey

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat is a holiday home in Odyssey, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat is a holiday home in Odyssey, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,414.

From$345/night
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Pet-friendly vacation rentals in Odyssey, MD

Bring your pet along with stays that welcome four-legged travelers.

Lovely bay views with kayaks, bikes, fire pit, crabbing & more - Odyssey, MD

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Holiday Home, Odyssey

Lovely bay views with kayaks, bikes, fire pit, crabbing & more is a holiday home in Odyssey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

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About Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more is a holiday home in Odyssey, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,075.

From$296/night
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Family Home on Mayo Peninsula | Deck | Sleeps 10 - Odyssey, MD

Family Home on Mayo Peninsula | Deck | Sleeps 10

Holiday Home, Odyssey

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Odyssey, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Odyssey, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,579.

From$368/night
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Plum Point Cottage #21 - Odyssey, MD

Plum Point Cottage #21

Holiday Home, Odyssey

Plum Point Cottage #21 is a holiday home in Odyssey, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Plum Point Cottage #21

Plum Point Cottage #21 is a holiday home in Odyssey, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,759.

From$394/night
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Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay - Odyssey, MD

Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay

Holiday Home, Odyssey

Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay is a holiday home in Odyssey, with pet-friendly space, easy beach access, and parking. This stay gives…

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About Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay

Walking distance to Herrington on the Bay! Home with views of the Chesapeake Bay is a holiday home in Odyssey, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,857.

From$408/night
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Vacation rentals with a kitchen in Odyssey, MD

Compare stays with kitchen access for longer trips and easier meals.

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Odyssey, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Odyssey

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Odyssey, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

Read more

About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Odyssey, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,520.

From$217/night
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5 Mi to Show Place Arena: Quiet Townhome w/ Patio - Odyssey, MD

5 Mi to Show Place Arena: Quiet Townhome w/ Patio

Holiday Home, Odyssey

5 Mi to Show Place Arena: Quiet Townhome w/ Patio is a holiday home in Odyssey, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 5 Mi to Show Place Arena: Quiet Townhome w/ Patio

5 Mi to Show Place Arena: Quiet Townhome w/ Patio is a holiday home in Odyssey, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,828.

From$261/night
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Enchanting West River Retreat - Odyssey, MD

Enchanting West River Retreat

Cottage, Odyssey

Enchanting West River Retreat is a cottage in Odyssey, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Enchanting West River Retreat

Enchanting West River Retreat is a cottage in Odyssey, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,905.

From$415/night
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Waterfront, Private Beach, Peaceful Family Getaway - Odyssey, MD

Waterfront, Private Beach, Peaceful Family Getaway

Holiday Home, Odyssey

Waterfront, Private Beach, Peaceful Family Getaway is a holiday home in Odyssey, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Waterfront, Private Beach, Peaceful Family Getaway

Waterfront, Private Beach, Peaceful Family Getaway is a holiday home in Odyssey, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,305.

From$472/night
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Family-friendly vacation rentals in Odyssey, MD

Plan a trip with stays that give families more room to spread out.

Charming 1-bedroom cottage with AC in cozy Harwood - Odyssey, MD

Charming 1-bedroom cottage with AC in cozy Harwood

Cottage, Odyssey

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Odyssey, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Charming 1-bedroom cottage with AC in cozy Harwood

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Odyssey, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,337.

From$191/night
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Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. - Odyssey, MD

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Cottage, Odyssey

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. is a cottage in Odyssey, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. is a cottage in Odyssey, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,892.

From$270/night
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Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK - Odyssey, MD

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Cottage, Odyssey

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK is a cottage in Odyssey, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK is a cottage in Odyssey, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,328.

From$333/night
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Plum Point Cottage #1 - Odyssey, MD

Plum Point Cottage #1

Holiday Home, Odyssey

Plum Point Cottage #1 is a holiday home in Odyssey, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Plum Point Cottage #1

Plum Point Cottage #1 is a holiday home in Odyssey, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,352.

From$336/night
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