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Oakland Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Oakland

Fridge, microwave, oven, stovetop
Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Oakland
10.0 out of 10, Exceptional, (51)
"This house was actually as beautiful as the pictures! We had a great stay and hope to return in the future."
United States
Sandra R.
Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip
Terrace/patio
Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

Oakland
10.0 out of 10, Exceptional, (84)
"As advertised! Very comfortable. A wonderful getaway!"
United States
Joanna C.
Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing
Property grounds
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

2.0 star property
Oakland
10.0 out of 10, Exceptional, (12)
"Nothing negative to say. Beautiful place and friendly owner. Owner is accessible and very accommodating. "
United States
Sean
The price is HK$1,672
HK$5,635 total
includes taxes & fees
4 Dec - 5 Dec
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Exterior
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Oakland
10.0 out of 10, Exceptional, (41)
"The property was beautiful and we had a very relaxing stay"
United States
Courtney U.
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
Fridge, microwave, oven, stovetop
Level lakefront, family-friendly, hot tub, low fees, private dock

Level lakefront, family-friendly, hot tub, low fees, private dock

Paradise Point
10.0 out of 10, Exceptional, (116)
"Relaxing lake home in a quiet cove. Conveniently located. Clean and comfortable."
United States
Mary M.
Level lakefront, family-friendly, hot tub, low fees, private dock
Exterior
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Oakland
9.8 out of 10, Exceptional, (261)
"Very homey and great layout! Already planning on coming back!"
United States
Agnes H.
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek
Terrace/patio
Amazing Central Location! Lakefront! Hot tub/dock!

Amazing Central Location! Lakefront! Hot tub/dock!

Oakland
9.6 out of 10, Exceptional, (54)
"A great backdrop for a mini family reunion."
United States
Nora V.
Amazing Central Location! Lakefront! Hot tub/dock!
Exterior
The winter is coming !!!

The winter is coming !!!

Oakland
9.8 out of 10, Exceptional, (47)
"Very easy to check in and out! Thank you! "
United States
Edward
The price is HK$1,393
HK$3,421 total
includes taxes & fees
15 Dec - 16 Dec
The winter is coming !!!
Microwave, oven, stovetop, dishwasher
3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD

3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD

Oakland
10.0 out of 10, Exceptional, (2)
"Perfect location for our anniversary trip. "
United States
Natalie M.
3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD
Smart TV, fireplace, DVD player, books
Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!

Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!

Oakland
10.0 out of 10, Exceptional, (109)
"Fantastic week at a fantastic cabin!"
United States
Karen H.
Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!
TV, fireplace, books
5BR lakefront retreat with hot tub, sauna, & dock

5BR lakefront retreat with hot tub, sauna, & dock

Oakland
8.6 out of 10, Excellent, (12)
"In town to celebrate daughter Graduating from college! Great house, beds so comfy!!! House had all we needed & views are amazing! "
United States
B.J. B.
5BR lakefront retreat with hot tub, sauna, & dock
Terrace/patio
EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

Oakland
10.0 out of 10, Exceptional, (8)
"Super comfortable, clean, beautiful, thoughtful and stylish design, good location, nice size for a small family. It’s the best place I have ever stayed. We will definitely come back again!"
United States
Kaoru M.
EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub
Outdoor spa tub
New: Lakefront Luxury Home with Private Indoor Heated Pool!

New: Lakefront Luxury Home with Private Indoor Heated Pool!

Oakland
9.6 out of 10, Exceptional, (15)
"House was great! Large enough for our big group "
United States
Jodi P.
New: Lakefront Luxury Home with Private Indoor Heated Pool!
Outdoor dining
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Oakland
8.4 out of 10, Very good, (63)
"We had a great time and the place was exactly as advertised, it was perfect."
United States
John K.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Interior
Cozy Dog Friendly Cabin w/ Hot Tub & Lake Access

Cozy Dog Friendly Cabin w/ Hot Tub & Lake Access

Oakland
9.2 out of 10, Wonderful, (15)
"Our family had a wonderful time! Great spot, easy check in and out. Only downside is how close you are to the highway, there is some road noise. "
United States
Joanna Z.
Cozy Dog Friendly Cabin w/ Hot Tub & Lake Access
Outdoor spa tub
Serene Mountain Escape: Hot Tub, Foosball, Views

Serene Mountain Escape: Hot Tub, Foosball, Views

Oakland
9.6 out of 10, Exceptional, (15)
"Great place to stay for a bachelor party weekend! Host was easy to contact, accommodating and made the check in process insanely easy. "
United States
Sean M.
Serene Mountain Escape: Hot Tub, Foosball, Views
Terrace/patio
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Oakland
10.0 out of 10, Exceptional, (34)
"Great property, loved our stay here! We will definitely stay here again! "
United States
Shawnnelle H.
The price is HK$1,851
HK$5,589 total
includes taxes & fees
18 Dec - 19 Dec
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
Interior
Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View

Oakland
10.0 out of 10, Exceptional, (1)
"Great place for a quick getaway ski trip to Wisp"
United States
William A.
The price is HK$1,599
HK$2,037 total
includes taxes & fees
30 Nov - 1 Dec
Suites at Silver Tree: A118 Studio Standard View
Outdoor dining
Lakefront Chalet w/ Pool, Private Dock, & Hot Tub

Lakefront Chalet w/ Pool, Private Dock, & Hot Tub

OAKLAND
7.6 out of 10, Good, (4)
"Property did not match pictures much repair needed over priced location great view not awesome! so easy to fix. rental co threw in last minute paperwork and confrontational on solving loved deep creek would choose other property and go thru local co directly as vrbo was no help and just added to cost"
United States
Terence M.
Lakefront Chalet w/ Pool, Private Dock, & Hot Tub
Terrace/patio
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Oakland
10.0 out of 10, Exceptional, (31)
"Had a great visit, perfect for 2 people dogs. Great location, we loved the fireplace and the record player! Host was very responsive before ending visit."
United States
Lauren W.
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakland Hotel Reviews

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

10/10 Excellent
"Shawn was an incredibly attentive and thoughtful host and the property was even better than expected. Exceptionally clean with so much space and considerate touches for families! Super close to Deep Creek and Wisp (8 minutes max) but we just loved being together in a comfy, cozy cabin! The hot tub was new and very well-kept and S’mores at the lovely fire pit were a fave! This was a last minute choice as another host cancelled our reservation (we’d made two months before) two days before our trip (!!!!) and we feel like we LUCKED OUT because this was such a lovely “substitute” We could NOT have been happier! A winning property for sure; you won’t be disappointed!"
Lori E. 3-night trip
Posted 3 days ago
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Oakland. Make sure you have time to check out the ski areas and ecotours during your trip.

What are some of the best holiday rentals that Oakland has to offer?

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing : This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Our travellers also rate Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip as a favourite home for rent in Oakland.

How many holiday rentals are there in Oakland?

With 468 Expedia holiday rentals, you're guaranteed to find just the right place for your Oakland stay.

What’s there to see and do in Oakland?

Deep Creek Lake and Youghiogheny River are a couple of lovely local spots to get outside and enjoy nature. Herrington Manor State Park and Swallow Falls State Park are other places to visit while you're in town.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.