Vacation rentals in Oakland, MD

102 available vacation rental offers

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Best vacation rentals and Airbnb offers in Oakland, MD

Cozy Cabin Rental in the Woods near Swallow Falls State Park, Maryland - Oakland, MD

Cozy Cabin Rental in the Woods near Swallow Falls State Park, Maryland

Holiday Home, Oakland

Cozy Cabin Rental in the Woods near Swallow Falls State Park, Maryland is a holiday home in Oakland, with pet-friendly space and room for a group. This stay gives travelers a comfortable…

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About Cozy Cabin Rental in the Woods near Swallow Falls State Park, Maryland

Cozy Cabin Rental in the Woods near Swallow Falls State Park, Maryland is a holiday home in Oakland, with pet-friendly space 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, fireplace, and family friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $850.

From$121/night
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Gorgeous Cabin Rental for a Getaway near Oakland, Maryland - Oakland, MD

Gorgeous Cabin Rental for a Getaway near Oakland, Maryland

Holiday Home, Oakland

Gorgeous Cabin Rental for a Getaway near Oakland, Maryland is a holiday home in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Gorgeous Cabin Rental for a Getaway near Oakland, Maryland

Gorgeous Cabin Rental for a Getaway near Oakland, Maryland is a holiday home in Oakland, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $850.

From$121/night
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Couples Retreat: The HayLoft- Rustic Escape For 2 - Oakland, MD

Couples Retreat: The HayLoft- Rustic Escape For 2

Country House, Oakland

Couples Retreat: The HayLoft- Rustic Escape For 2 is a country house in Oakland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Couples Retreat: The HayLoft- Rustic Escape For 2

Couples Retreat: The HayLoft- Rustic Escape For 2 is a country house in Oakland, 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 $1,053.

From$150/night
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Meant to Be by Taylor Made Deep Creek - Oakland, MD

Meant to Be by Taylor Made Deep Creek

Cabin, Oakland

Meant to Be by Taylor Made Deep Creek is a cabin in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Meant to Be by Taylor Made Deep Creek

Meant to Be by Taylor Made Deep Creek is a cabin in Oakland, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,369.

From$166/night
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Vacation rentals with a pool in Oakland, MD

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

Breathtaking Lake Views Walk to Alpine Lake - Oakland, MD

Breathtaking Lake Views Walk to Alpine Lake

Cottage, Oakland

Breathtaking Lake Views Walk to Alpine Lake is a cottage in Oakland, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Breathtaking Lake Views Walk to Alpine Lake

Breathtaking Lake Views Walk to Alpine Lake is a cottage in Oakland, 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 $1,763.

From$210/night
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Breathtaking Lake Views | Walk to Alpine Lake - Oakland, MD

Breathtaking Lake Views | Walk to Alpine Lake

Cabin, Oakland

Breathtaking Lake Views · Walk to Alpine Lake is a cabin in Oakland, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Breathtaking Lake Views | Walk to Alpine Lake

Breathtaking Lake Views · Walk to Alpine Lake is a cabin in Oakland, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,516.

From$217/night
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Lovely Terra Alta Cabin < 1 Mi to Alpine Lake - Oakland, MD

Lovely Terra Alta Cabin < 1 Mi to Alpine Lake

Cabin, Oakland

Lovely Terra Alta Cabin < 1 Mi to Alpine Lake is a cabin in Oakland, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lovely Terra Alta Cabin < 1 Mi to Alpine Lake

Lovely Terra Alta Cabin < 1 Mi to Alpine Lake is a cabin in Oakland, 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 $1,817.

From$260/night
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Sunrise by Taylor Made Deep Creek - Oakland, MD

Sunrise by Taylor Made Deep Creek

Cottage, Oakland

Sunrise by Taylor Made Deep Creek is a cottage in Oakland, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sunrise by Taylor Made Deep Creek

Sunrise by Taylor Made Deep Creek is a cottage in Oakland, 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 $3,208.

From$265/night
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Vacation rentals with parking in Oakland, MD

Find vacation rentals that make arriving by car easier.

Four Hooppole South G6 by Taylor Made Deep Creek - Oakland, MD

Four Hooppole South G6 by Taylor Made Deep Creek

Holiday Home, Oakland

Four Hooppole South G6 by Taylor Made Deep Creek is a holiday home in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Four Hooppole South G6 by Taylor Made Deep Creek

Four Hooppole South G6 by Taylor Made Deep Creek is a holiday home in Oakland, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,903.

From$160/night
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Tranquil Dreams by Taylor Made Deep Creek - Oakland, MD

Tranquil Dreams by Taylor Made Deep Creek

Cottage, Oakland

Tranquil Dreams by Taylor Made Deep Creek is a cottage in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Tranquil Dreams by Taylor Made Deep Creek

Tranquil Dreams by Taylor Made Deep Creek is a cottage in Oakland, 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 $2,488.

From$205/night
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Private Family Home w/ Deck, Porch + Forest Views! - Oakland, MD

Private Family Home w/ Deck, Porch + Forest Views!

Holiday Home, Oakland

Private Family Home w/ Deck, Porch + Forest Views! is a holiday home in Oakland, with outdoor space, parking, and room for a group. This stay gives travelers a comfortable base for…

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About Private Family Home w/ Deck, Porch + Forest Views!

Private Family Home w/ Deck, Porch + Forest Views! is a holiday home in Oakland, with outdoor space, parking, 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, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,131.

From$211/night
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Four Hooppole South G6 | Lakefront Views + Access to Beach Area & Dock! - Oakland, MD

Four Hooppole South G6 | Lakefront Views + Access to Beach Area & Dock!

Holiday Home, Oakland

Four Hooppole South G6 · Lakefront Views + Access to Beach Area & Dock! is a holiday home in Oakland, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Four Hooppole South G6 | Lakefront Views + Access to Beach Area & Dock!

Four Hooppole South G6 · Lakefront Views + Access to Beach Area & Dock! is a holiday home in Oakland, 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 free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,677.

From$240/night
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Pet-friendly vacation rentals in Oakland, MD

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

Mountain Escape w/ Hot Tub, Trails & ATV Access - Oakland, MD

Mountain Escape w/ Hot Tub, Trails & ATV Access

Holiday Home, Oakland

Mountain Escape w/ Hot Tub, Trails & ATV Access is a holiday home in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Mountain Escape w/ Hot Tub, Trails & ATV Access

Mountain Escape w/ Hot Tub, Trails & ATV Access is a holiday home in Oakland, 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,749.

From$250/night
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Dog Friendly Deep Creek Getaway w/ Hot Tub - Oakland, MD

Dog Friendly Deep Creek Getaway w/ Hot Tub

Holiday Home, Oakland

Dog Friendly Deep Creek Getaway w/ Hot Tub is a holiday home in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Dog Friendly Deep Creek Getaway w/ Hot Tub

Dog Friendly Deep Creek Getaway w/ Hot Tub is a holiday home in Oakland, 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,810.

From$259/night
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Cabin at Alpine Lake, near Deep Creek/WISP Resort - Oakland, MD

Cabin at Alpine Lake, near Deep Creek/WISP Resort

Holiday Home, Oakland

Cabin at Alpine Lake, near Deep Creek/WISP Resort is a holiday home in Oakland, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Cabin at Alpine Lake, near Deep Creek/WISP Resort

Cabin at Alpine Lake, near Deep Creek/WISP Resort is a holiday home in Oakland, with pet-friendly space and 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,852.

From$265/night
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Secluded Oakland Gem w/ Hot Tub: Dogs Welcome! - Oakland, MD

Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!

Holiday Home, Oakland

Secluded Oakland Gem w/ Hot Tub: Dogs Welcome! is a holiday home in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!

Secluded Oakland Gem w/ Hot Tub: Dogs Welcome! is a holiday home in Oakland, 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 $1,873.

From$268/night
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Vacation rentals with a kitchen in Oakland, MD

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

Private Family Home w/ Deck, Porch + Forest Views! - Oakland, MD

Private Family Home w/ Deck, Porch + Forest Views!

Cottage, Oakland

Private Family Home w/ Deck, Porch + Forest Views! is a cottage in Oakland, with outdoor space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About Private Family Home w/ Deck, Porch + Forest Views!

Private Family Home w/ Deck, Porch + Forest Views! is a cottage in Oakland, with outdoor 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,213.

From$247/night
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Close to everything DCL, fun for the whole family - Oakland, MD

Close to everything DCL, fun for the whole family

Cottage, Oakland

Close to everything DCL, fun for the whole family is a cottage in Oakland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Close to everything DCL, fun for the whole family

Close to everything DCL, fun for the whole family is a cottage in Oakland, 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 $1,824.

From$261/night
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Private Family Home w/ Deck, Porch + Forest Views! - Oakland, MD

Private Family Home w/ Deck, Porch + Forest Views!

Holiday Home, Oakland

Private Family Home w/ Deck, Porch + Forest Views! is a holiday home in Oakland, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Private Family Home w/ Deck, Porch + Forest Views!

Private Family Home w/ Deck, Porch + Forest Views! is a holiday home in Oakland, 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 $1,907.

From$272/night
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Lovely Terra Alta Cabin < 1 Mi to Alpine Lake - Oakland, MD

Lovely Terra Alta Cabin < 1 Mi to Alpine Lake

Cottage, Oakland

Lovely Terra Alta Cabin < 1 Mi to Alpine Lake is a cottage in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Lovely Terra Alta Cabin < 1 Mi to Alpine Lake

Lovely Terra Alta Cabin < 1 Mi to Alpine Lake is a cottage in Oakland, 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 $2,250.

From$282/night
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Family-friendly vacation rentals in Oakland, MD

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

Bearbnb by Taylor Made Deep Creek - Oakland, MD

Bearbnb by Taylor Made Deep Creek

Cottage, Oakland

Bearbnb by Taylor Made Deep Creek is a cottage in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Bearbnb by Taylor Made Deep Creek

Bearbnb by Taylor Made Deep Creek is a cottage in Oakland, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,017.

From$145/night
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Canopy Escape by Taylor Made Deep Creek - Oakland, MD

Canopy Escape by Taylor Made Deep Creek

Cottage, Oakland

Canopy Escape by Taylor Made Deep Creek is a cottage in Oakland, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Canopy Escape by Taylor Made Deep Creek

Canopy Escape by Taylor Made Deep Creek is a cottage in Oakland, 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,647.

From$196/night
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Knotty Pines by Taylor Made Deep Creek - Oakland, MD

Knotty Pines by Taylor Made Deep Creek

Cottage, Oakland

Knotty Pines by Taylor Made Deep Creek is a cottage in Oakland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Knotty Pines by Taylor Made Deep Creek

Knotty Pines by Taylor Made Deep Creek is a cottage in Oakland, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,524.

From$197/night
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Wooded Bliss by Taylor Made Deep Creek - Oakland, MD

Wooded Bliss by Taylor Made Deep Creek

Cottage, Oakland

Wooded Bliss by Taylor Made Deep Creek is a cottage in Oakland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Wooded Bliss by Taylor Made Deep Creek

Wooded Bliss by Taylor Made Deep Creek is a cottage in Oakland, 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, fireplace, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,367.

From$203/night
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