Vacation rentals in Shady Side, MD

69 available vacation rental offers

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Best vacation rentals and Airbnb offers in Shady Side, MD

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

1 Mi to Boardwalk: Convenient North Beach Apt!

Apartment, Shady Side

1 Mi to Boardwalk: Convenient North Beach Apt! is a apartment in Shady Side, 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 Shady Side, 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' - Shady Side, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Shady Side

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Shady Side, 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 Shady Side, 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! - Shady Side, MD

1 Mi to Boardwalk: Convenient North Beach Apt!

Apartment, Shady Side

1 Mi to Boardwalk: Convenient North Beach Apt! is a apartment in Shady Side, with pet-friendly space, easy beach access, and parking. 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 Shady Side, 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 - Shady Side, MD

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

Apartment, Shady Side

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Shady Side, 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 Shady Side, 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 Shady Side, MD

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

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. - Shady Side, MD

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

Cottage, Shady Side

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. is a cottage in Shady Side, 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 Shady Side, 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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Cottage 1A-Charming 1-bedroom cottage on the water, minutes from St Michaels MD - Shady Side, MD

Cottage 1A-Charming 1-bedroom cottage on the water, minutes from St Michaels MD

Cottage, Shady Side

Cottage 1A-Charming 1-bedroom cottage on the water, minutes from St Michaels MD is a cottage in Shady Side, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Cottage 1A-Charming 1-bedroom cottage on the water, minutes from St Michaels MD

Cottage 1A-Charming 1-bedroom cottage on the water, minutes from St Michaels MD is a cottage in Shady Side, 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 $2,247.

From$321/night
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42 Acres of Serenity & Nature Just 15 Miles To Annapolis - Shady Side, MD

42 Acres of Serenity & Nature Just 15 Miles To Annapolis

Holiday Home, Shady Side

42 Acres of Serenity & Nature Just 15 Miles To Annapolis is a holiday home in Shady Side, 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 Shady Side, 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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The Inn at Tacaro Estate - Shady Side, MD

The Inn at Tacaro Estate

B & B, Shady Side

The Inn at Tacaro Estate is a b & b in Shady Side, 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 Shady Side, 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 Shady Side, MD

Find vacation rentals that make arriving by car easier.

Guest Quarters at the Inn - 101 - Shady Side, MD

Guest Quarters at the Inn - 101

Apartment, Shady Side

Guest Quarters at the Inn - 101 is a apartment in Shady Side, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Guest Quarters at the Inn - 101

Guest Quarters at the Inn - 101 is a apartment in Shady Side, 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 cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,390.

From$199/night
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Guest Quarters at the Inn - 102 - Shady Side, MD

Guest Quarters at the Inn - 102

Apartment, Shady Side

Guest Quarters at the Inn - 102 is a apartment in Shady Side, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Guest Quarters at the Inn - 102

Guest Quarters at the Inn - 102 is a apartment in Shady Side, 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 cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,390.

From$199/night
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Guest Quarters at the Inn - 103 - Shady Side, MD

Guest Quarters at the Inn - 103

Apartment, Shady Side

Guest Quarters at the Inn - 103 is a apartment in Shady Side, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Guest Quarters at the Inn - 103

Guest Quarters at the Inn - 103 is a apartment in Shady Side, 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 cancellation, hot tub, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,390.

From$199/night
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Guest quarters at the inn - 204 - Shady Side, MD

Guest quarters at the inn - 204

Apartment, Shady Side

Guest quarters at the inn - 204 is a apartment in Shady Side, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Guest quarters at the inn - 204

Guest quarters at the inn - 204 is a apartment in Shady Side, 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 $1,714.

From$245/night
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Pet-friendly vacation rentals in Shady Side, MD

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

Pet-Friendly Summer Retreat on Tilghman - Shady Side, MD

Pet-Friendly Summer Retreat on Tilghman

Holiday Home, Shady Side

Pet-Friendly Summer Retreat on Tilghman is a holiday home in Shady Side, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Pet-Friendly Summer Retreat on Tilghman

Pet-Friendly Summer Retreat on Tilghman is a holiday home in Shady Side, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,908.

From$273/night
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Renovated Bungalow | Walk to Beach | Dog-Friendly - Shady Side, MD

Renovated Bungalow | Walk to Beach | Dog-Friendly

Holiday Home, Shady Side

Renovated Bungalow · Walk to Beach · Dog-Friendly is a holiday home in Shady Side, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow · Walk to Beach · Dog-Friendly is a holiday home in Shady Side, 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 $2,160.

From$309/night
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Londontowne Rancher | 3BR | Near Waterfront - Shady Side, MD

Londontowne Rancher | 3BR | Near Waterfront

Holiday Home, Shady Side

Londontowne Rancher · 3BR · Near Waterfront is a holiday home in Shady Side, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher · 3BR · Near Waterfront is a holiday home in Shady Side, 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 $2,524.

From$361/night
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Family Home on Mayo Peninsula | Deck | Sleeps 10 - Shady Side, MD

Family Home on Mayo Peninsula | Deck | Sleeps 10

Holiday Home, Shady Side

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Shady Side, 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 Shady Side, 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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Vacation rentals with a kitchen in Shady Side, MD

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

Studio Apartment in Downtown Annapolis - Shady Side, MD

Studio Apartment in Downtown Annapolis

Apartment, Shady Side

Studio Apartment in Downtown Annapolis is a apartment in Shady Side, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Studio Apartment in Downtown Annapolis

Studio Apartment in Downtown Annapolis is a apartment in Shady Side, with 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,686.

From$241/night
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Relax on Kent Island in a 4 Bedroom Home w/Waterview! - Shady Side, MD

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

Holiday Home, Shady Side

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in Shady Side, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in Shady Side, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,378.

From$340/night
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Rose Haven Peaceful, Spacious, 3 Bedroom Retreat - Shady Side, MD

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Holiday Home, Shady Side

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

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About Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat is a holiday home in Shady Side, 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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Edgewater's Shelby on the Bay - Shady Side, MD

Edgewater's Shelby on the Bay

Holiday Home, Shady Side

Edgewater's Shelby on the Bay is a holiday home in Shady Side, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Edgewater's Shelby on the Bay

Edgewater's Shelby on the Bay is a holiday home in Shady Side, 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, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,374.

From$482/night
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Family-friendly vacation rentals in Shady Side, MD

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

Updated North Beach Cottage: Pet Friendly! - Shady Side, MD

Updated North Beach Cottage: Pet Friendly!

Cottage, Shady Side

Updated North Beach Cottage: Pet Friendly! is a cottage in Shady Side, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly! is a cottage in Shady Side, 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 $2,250.

From$256/night
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Tilghman Island Retreat By Knapps Narrows! - Shady Side, MD

Tilghman Island Retreat By Knapps Narrows!

Cottage, Shady Side

Tilghman Island Retreat By Knapps Narrows! is a cottage in Shady Side, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Tilghman Island Retreat By Knapps Narrows!

Tilghman Island Retreat By Knapps Narrows! is a cottage in Shady Side, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,188.

From$256/night
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Updated North Beach Cottage: Pet Friendly! - Shady Side, MD

Updated North Beach Cottage: Pet Friendly!

Cottage, Shady Side

Updated North Beach Cottage: Pet Friendly! is a cottage in Shady Side, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

Read more

About Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly! is a cottage in Shady Side, 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 $1,824.

From$261/night
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Luxury 5-Star Chesapeake Bay Waterfront Home - Shady Side, MD

Luxury 5-Star Chesapeake Bay Waterfront Home

Holiday Home, Shady Side

Luxury 5-Star Chesapeake Bay Waterfront Home is a holiday home in Shady Side, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Luxury 5-Star Chesapeake Bay Waterfront Home

Luxury 5-Star Chesapeake Bay Waterfront Home is a holiday home in Shady Side, with 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, hot tub, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,084.

From$583/night
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