Vacation rentals in Oakland, MD

53 available vacation rental offers

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Best vacation rentals and Airbnb offers in Oakland, MD

Hike, Ski & Raft: Terra Alta Cabin w/ Large Deck - Oakland, MD
10 ★ 2 reviews

Hike, Ski & Raft: Terra Alta Cabin w/ Large Deck

Cottage, Oakland

Hike, Ski & Raft: Terra Alta Cabin w/ Large Deck is a cottage in Oakland, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Hike, Ski & Raft: Terra Alta Cabin w/ Large Deck

Hike, Ski & Raft: Terra Alta Cabin w/ Large Deck is a cottage in Oakland, with pool access, outdoor 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, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,605.

From$173/night
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Breathtaking Lake Views Walk to Alpine Lake - Oakland, MD
10 ★ 2 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,601.

From$188/night
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Private Family Home w/ Deck, Porch + Forest Views! - Oakland, MD
10 ★ 1 reviews

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…

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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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,167.

From$241/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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,086.

From$205/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.

American Pride by Taylor Made Deep Creek - Oakland, MD
6 ★ 1 reviews

American Pride by Taylor Made Deep Creek

Cottage, Oakland

American Pride 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 American Pride by Taylor Made Deep Creek

American Pride 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,567.

From$276/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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,722.

From$216/night
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Bear Foot Cove - Oakland, MD

Bear Foot Cove

Cottage, Oakland

Bear Foot Cove 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…

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About Bear Foot Cove

Bear Foot Cove 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,397.

From$244/night
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Just About Paradise by Taylor Made Deep Creek - Oakland, MD

Just About Paradise by Taylor Made Deep Creek

Cottage, Oakland

Just About Paradise by Taylor Made Deep Creek is a cottage 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 Just About Paradise by Taylor Made Deep Creek

Just About Paradise by Taylor Made Deep Creek is a cottage 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,193.

From$247/night
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Pet-friendly vacation rentals in Oakland, MD

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

Smore Fun - Oakland, MD

Smore Fun

Holiday Home, Oakland

Smore Fun 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…

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About Smore Fun

Smore Fun 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,998.

From$250/night
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Windsor House by Taylor Made Deep Creek - Oakland, MD

Windsor House by Taylor Made Deep Creek

Cabin, Oakland

Windsor House by Taylor Made Deep Creek is a cabin in Oakland, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Windsor House by Taylor Made Deep Creek

Windsor House by Taylor Made Deep Creek is a cabin in Oakland, with pet-friendly space. 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, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,873.

From$209/night
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The Quarterdeck by Taylor Made Deep Creek - Oakland, MD

The Quarterdeck by Taylor Made Deep Creek

Cottage, Oakland

The Quarterdeck by Taylor Made Deep Creek is a cottage in Oakland, with pet-friendly space and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Quarterdeck by Taylor Made Deep Creek

The Quarterdeck by Taylor Made Deep Creek is a cottage in Oakland, with pet-friendly space and outdoor space. 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, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,528.

From$293/night
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Fancy Free by Taylor Made Deep Creek - Oakland, MD

Fancy Free by Taylor Made Deep Creek

Cottage, Oakland

Fancy Free by Taylor Made Deep Creek is a cottage 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 Fancy Free by Taylor Made Deep Creek

Fancy Free by Taylor Made Deep Creek is a cottage 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,982.

From$309/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.

1 Mi to Resort Beach: Alpine Lake A-frame! - Oakland, MD

1 Mi to Resort Beach: Alpine Lake A-frame!

Cottage, Oakland

1 Mi to Resort Beach: Alpine Lake A-frame! is a cottage in Oakland, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 1 Mi to Resort Beach: Alpine Lake A-frame!

1 Mi to Resort Beach: Alpine Lake A-frame! is a cottage in Oakland, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,461.

From$274/night
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Heavenly Grove by Taylor Made Deep Creek - Oakland, MD

Heavenly Grove by Taylor Made Deep Creek

Holiday Home, Oakland

Heavenly Grove by Taylor Made Deep Creek is a holiday home 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 Heavenly Grove by Taylor Made Deep Creek

Heavenly Grove by Taylor Made Deep Creek is a holiday home 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,014.

From$311/night
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Sunrise - Oakland, MD

Sunrise

Holiday Home, Oakland

Sunrise is a holiday home in Oakland, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Sunrise

Sunrise is a holiday home in Oakland, with pool 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, pool, free wifi, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,781.

From$349/night
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Nature's Retreat by Taylor Made Deep Creek - Oakland, MD

Nature's Retreat by Taylor Made Deep Creek

Cottage, Oakland

Nature's Retreat by Taylor Made Deep Creek is a cottage in Oakland, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Nature's Retreat by Taylor Made Deep Creek

Nature's Retreat by Taylor Made Deep Creek is a cottage in Oakland, with pool 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, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,837.

From$409/night
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Vacation rentals with parking in Oakland, MD

Find vacation rentals that make arriving by car easier.

Home Sweet Cabin - Oakland, MD

Home Sweet Cabin

Holiday Home, Oakland

Home Sweet Cabin is a holiday home in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Home Sweet Cabin

Home Sweet Cabin is a holiday home in Oakland, 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, paid parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,890.

From$237/night
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Wooded Bliss - Oakland, MD

Wooded Bliss

Holiday Home, Oakland

Wooded Bliss is a holiday home in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Wooded Bliss

Wooded Bliss is a holiday home in Oakland, 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, paid parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,075.

From$260/night
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By the Stream - Oakland, MD

By the Stream

Holiday Home, Oakland

By the Stream is a holiday home in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About By the Stream

By the Stream is a holiday home in Oakland, 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, paid parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,887.

From$236/night
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Lake House by Taylor Made Deep Creek - Oakland, MD

Lake House by Taylor Made Deep Creek

Cottage, Oakland

Lake House 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 Lake House by Taylor Made Deep Creek

Lake House 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,313.

From$271/night
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Vacation rentals with a kitchen in Oakland, MD

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

Space Mountain by Taylor Made Deep Creek - Oakland, MD

Space Mountain by Taylor Made Deep Creek

Cottage, Oakland

Space Mountain 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 Space Mountain by Taylor Made Deep Creek

Space Mountain 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,394.

From$269/night
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Sunset Bluff by Taylor Made Deep Creek - Oakland, MD

Sunset Bluff by Taylor Made Deep Creek

Cottage, Oakland

Sunset Bluff 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 Sunset Bluff by Taylor Made Deep Creek

Sunset Bluff 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,525.

From$276/night
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Blue Horizon by Taylor Made Deep Creek - Oakland, MD

Blue Horizon by Taylor Made Deep Creek

Cottage, Oakland

Blue Horizon 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 Blue Horizon by Taylor Made Deep Creek

Blue Horizon 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,097.

From$279/night
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All About the View by Taylor Made Deep Creek - Oakland, MD

All About the View by Taylor Made Deep Creek

Cottage, Oakland

All About the View 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 All About the View by Taylor Made Deep Creek

All About the View 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,891.

From$322/night
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