Title: Oakland Vacation Rentals from CA $679: Short-Term Rentals for 2026 | Expedia.ca

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![Waterfall at Swallow Falls](https://images.trvl-media.com/place/9160/b8baa833-4ced-4ac5-b870-e726bd5ccf56.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Jenn Charbonneau

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Oakland vacation rentals

![Property grounds](https://images.trvl-media.com/lodging/111000000/110320000/110311000/110310952/61c3068a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo](https://images.trvl-media.com/lodging/111000000/110320000/110311000/110310952/0a30e3bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110320000/110311000/110310952/c5bec381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/111000000/110320000/110311000/110310952/7df7b845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

[](https://www.expedia.ca/Oakland-Hotels-Deer-Pass-Luxury-Glamping-Yurt-Near-Deep-CreekMd.h110310952.Hotel-Information)

Oakland

10/10

Exceptional

(9 reviews)

"Great getaway"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Holly M.

CA $150

CA $323 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Oakland-Hotels-Deer-Pass-Luxury-Glamping-Yurt-Near-Deep-CreekMd.h110310952.Hotel-Information)

![Flat-screen TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383426/94b49fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383426/5b096cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383426/6457ab2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383426/a8321476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Suites at Silver Tree: A115 One Bedroom Lake View

[](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A115-One-Bedroom-Lake-View.h76383426.Hotel-Information)

Oakland

CA $338

CA $438 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A115-One-Bedroom-Lake-View.h76383426.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/07ac3aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/98df61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/88b8da13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/107000000/106260000/106251600/106251530/c709e08b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Oakland-Hotels-New-Listing-Victory-Cabin-Spacious.h106251530.Hotel-Information)

Oakland

10/10

Exceptional

(13 reviews)

"Great spot for a team retreat!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Garrett H.

CA $308

CA $1,015 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Oakland-Hotels-New-Listing-Victory-Cabin-Spacious.h106251530.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/w3600h2401x0y0-cb011654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, foosball](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/d67c6436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/89df50c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, foosball](https://images.trvl-media.com/lodging/106000000/105650000/105641600/105641553/6ac84ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger! 

[](https://www.expedia.ca/Oakland-Hotels-Cozy-Lake-Area-Cabin-Pet-Friendly-EV-Charger.h105641553.Hotel-Information)

Oakland

10/10

Exceptional

(22 reviews)

"We had an incredible time at the cabin and we're hoping to come back in the future. The house is BEAUTIFUL, the beds are comfortable, it's in a nice location, and the fire pit and hot tub were great as well. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Madeline C.

CA $245

CA $960 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Oakland-Hotels-Cozy-Lake-Area-Cabin-Pet-Friendly-EV-Charger.h105641553.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515341/16a77489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515341/b175e07a_edited_6725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515341/8e09a628_edited_6866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515341/67273f74_edited_ee80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Will O' The Wisp: 103A Efficiency/One Bath

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-103A-EfficiencyOne-Bath.h76515341.Hotel-Information)

Oakland

9.6/10

Exceptional

(9 reviews)

"We had a wonderful time. The place was beautiful and close to everything. Enjoyed the hot tub too! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Molly C.

CA $333

CA $430 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-103A-EfficiencyOne-Bath.h76515341.Hotel-Information)

![TV, fireplace, books](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/7ca08395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/149ddcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/9e2e051a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/5b6cf464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wooded Retreat w Hot Tub, Loft, Game Room & Sauna

[](https://www.expedia.ca/Oakland-Hotels-Wooded-Retreat-W-Hot-Tub.h115059189.Hotel-Information)

Oakland

10/10

Exceptional

(1 review)

"Wonderful place for the perfect getaway! Just like the photos definitely worth every penny. Just have in mind that you are in the woods so the bugs are inevitable but the inside of the place was very clean.Me and my family took advantage of all the amenities from the grill, hot tub, fire place. Don't think twice and book this place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bonny S.

CA $574

CA $1,151 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Oakland-Hotels-Wooded-Retreat-W-Hot-Tub.h115059189.Hotel-Information)

![Smart TV, video games](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/w1287h858x1y1-aa7e85fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/145d0abd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/w1287h858x1y1-a585753e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games](https://images.trvl-media.com/lodging/103000000/102130000/102120300/102120259/w1287h858x1y1-c8783464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### In the heart of Deep Creek Lake! - "Shamrock Inn"

[](https://www.expedia.ca/Oakland-Hotels-In-The-Heart-Of-Deep-Creek-Lake-Shamrock-Inn.h102120259.Hotel-Information)

Mountainside

9.6/10

Exceptional

(5 reviews)

"Place was absolutely gorgeous host was very accommodating. Can't say enough good things about it"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael M.

CA $257

CA $644 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Oakland-Hotels-In-The-Heart-Of-Deep-Creek-Lake-Shamrock-Inn.h102120259.Hotel-Information)

![Smart TV, fireplace, video-game console, DVD player](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/980971f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, soundproofing, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/4c3df84b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video-game console, DVD player](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/1ad72014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91130000/91123800/91123713/f1ba53ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee

[](https://www.expedia.ca/Oakland-Hotels-Unwind-At-Jamesons-Cabin-Pet-Friendly.h91123713.Hotel-Information)

Oakland

10/10

Exceptional

(35 reviews)

"Great property, loved our stay here! We will definitely stay here again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shawnnelle H.

CA $269

CA $820 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Oakland-Hotels-Unwind-At-Jamesons-Cabin-Pet-Friendly.h91123713.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/125000000/124820000/124815800/124815710/w1123h777x1y0-b26cbc11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/125000000/124820000/124815800/124815710/w1124h835x0y0-7953d05e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/125000000/124820000/124815800/124815710/7c0d6cb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124820000/124815800/124815710/w1123h788x0y0-03567eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2-bedroom log cabin oasis in soothing Deep Creek

[](https://www.expedia.ca/Oakland-Hotels-2-Bedroom-Log-Cabin-Oasis-In-Soothing-Deep-Creek.h124815710.Hotel-Information)

Oakland

CA $283

CA $500 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Oakland-Hotels-2-Bedroom-Log-Cabin-Oasis-In-Soothing-Deep-Creek.h124815710.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100860000/100856200/100856128/663df6f1_edited_80c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/101000000/100860000/100856200/100856128/8e6e3a46_edited_eb2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100860000/100856200/100856128/73596aa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100860000/100856200/100856128/d45089dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Will O' The Wisp: 107B One Bedroom/One Bath

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-107B-One-BedroomOne-Bath.h100856128.Hotel-Information)

Mountainside

10/10

Exceptional

(2 reviews)

"Great place to visit. Hope to come back next year"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stacy S.

CA $360

CA $465 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-107B-One-BedroomOne-Bath.h100856128.Hotel-Information)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/23000000/22630000/22624200/22624198/1bd56ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22630000/22624200/22624198/d1f7f369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22630000/22624200/22624198/0d835cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/23000000/22630000/22624200/22624198/cdc47fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The winter is coming !!!

[](https://www.expedia.ca/Cumberland-Hotels-Winter-Is-Coming.h22624198.Hotel-Information)

Oakland

9.8/10

Exceptional

(52 reviews)

"Very easy to check in and out! Thank you! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Edward

CA $306

CA $679 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Cumberland-Hotels-Winter-Is-Coming.h22624198.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/122000000/121020000/121013400/121013347/2b053ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/122000000/121020000/121013400/121013347/ab952cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121020000/121013400/121013347/d36494bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121020000/121013400/121013347/0b460712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Suites at Silver Tree: A124 Studio Standard View

[](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A124-Studio-Standard-View.h121013347.Hotel-Information)

Oakland

6.0/10

(1 review)

"The host was welcoming and for the most part the amenities were okay. The lobby of the hotel was absolutely beautiful. We had an initial issue with the fireplace, and the bathroom shower area was cold. The water would never get hot enough either. The television was in an awkward spot and the light from it interrupted our sleep. The refrigerator was too high up. We could not turn the tv optimally towards our bed. We loved Deep Creek Lake though, despite the weather it was still very beautiful,...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alvin H.

CA $299

CA $387 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A124-Studio-Standard-View.h121013347.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121310000/121302300/121302268/83ea0ed0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121310000/121302300/121302268/45b5b6a3_edited_c029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/122000000/121310000/121302300/121302268/4585fdd2_edited_10ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/122000000/121310000/121302300/121302268/aeadb701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Will O' The Wisp: 302B One Bedroom/One Bath

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-302B-One-BedroomOne-Bath.h121302268.Hotel-Information)

Oakland

CA $341

CA $441 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-302B-One-BedroomOne-Bath.h121302268.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/121000000/120880000/120875900/120875821/a13f4c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120880000/120875900/120875821/542780ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120880000/120875900/120875821/80e44933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120880000/120875900/120875821/0f9bd9f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakeview Chalet in Deep Creek Lake + Hot Tub

[](https://www.expedia.ca/Oakland-Hotels-Lakeview-Chalet-In-Deep-Creek-Lake-Hot-Tub.h120875821.Hotel-Information)

Oakland

CA $524

CA $1,133 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Oakland-Hotels-Lakeview-Chalet-In-Deep-Creek-Lake-Hot-Tub.h120875821.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/125000000/124510000/124506100/124506022/201de372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/125000000/124510000/124506100/124506022/c6480986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124510000/124506100/124506022/43ee2b4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124510000/124506100/124506022/92ef5d57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lake House at Silver Ridge

[](https://www.expedia.ca/Oakland-Hotels-The-Lake-House-At-Silver-Ridge.h124506022.Hotel-Information)

Silver Ridge

CA $625

CA $839 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Oakland-Hotels-The-Lake-House-At-Silver-Ridge.h124506022.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383493/95242996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383493/5a05b15d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383493/f7f33232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383493/ec239013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Suites at Silver Tree: A218 One Bedroom Standard View

[](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A218-One-Bedroom-Standard-View.h76383493.Hotel-Information)

Oakland

10/10

Exceptional

(3 reviews)

"Our one bedroom suite was clean and comfortably appointed, The lobby was beautiful and a lovely place to congregate. Staff were friendly."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ann Mahling

CA $283

CA $366 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A218-One-Bedroom-Standard-View.h76383493.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76520000/76515500/76515444/c5ed87af_edited_c829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/77000000/76520000/76515500/76515444/e26928a0_edited_46fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76520000/76515500/76515444/8c6f2dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76520000/76515500/76515444/149b901a_edited_821b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Will O' The Wisp: 208B One Bedroom/One Bath

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-208B-One-BedroomOne-Bath.h76515444.Hotel-Information)

Oakland

10/10

Exceptional

(1 review)

"The property was spotless and had everything needed! View from the patio was relaxing and proximity to restaurants was so convenient!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rebecca T.

CA $358

CA $463 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-208B-One-BedroomOne-Bath.h76515444.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515329/9e47b209_edited_de7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515329/94aebe68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515329/87969f3c_edited_17c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/77000000/76520000/76515400/76515329/00e024f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Will O' The Wisp: 102B One Bedroom/One Bath

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-102B-One-BedroomOne-Bath.h76515329.Hotel-Information)

Oakland

10/10

Exceptional

(4 reviews)

"Wonderful restful stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rose J.

CA $346

CA $446 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-102B-One-BedroomOne-Bath.h76515329.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76520000/76515500/76515441/93b1851e_edited_9d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76520000/76515500/76515441/b42dabca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/77000000/76520000/76515500/76515441/b3089c42_edited_c443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76520000/76515500/76515441/9c698426_edited_2de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Will O' The Wisp: 207B One Bedroom/One Bath

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-207B-One-BedroomOne-Bath.h76515441.Hotel-Information)

Oakland

10/10

Exceptional

(5 reviews)

"Very nice place."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ronald D.

CA $358

CA $463 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Oakland-Hotels-Will-O-The-Wisp-207B-One-BedroomOne-Bath.h76515441.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383428/ee2c9683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383428/494f9d63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383428/323f0562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/77000000/76390000/76383500/76383428/f1152c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Suites at Silver Tree: A116 One Bedroom Standard View

[](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A116-One-Bedroom-Standard-View.h76383428.Hotel-Information)

Oakland

8.0/10

Very good

(2 reviews)

"Super nice place and easy to get to many things."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

STEPHANIE R.

CA $281

CA $364 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Oakland-Hotels-Suites-At-Silver-Tree-A116-One-Bedroom-Standard-View.h76383428.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-22&endDate=2026-02-23&regionId=9160&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Aparthotels

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America&regionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Private vacation homes

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America&regionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CONDO)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America&regionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America&regionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CHALET)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America&regionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VILLA)

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## Top Oakland Hotel Reviews

![The Lake House- 5 bedroom in quiet area with hot tub and pool table](https://images.trvl-media.com/lodging/121000000/120050000/120048200/120048180/18d2a03b_y.jpg)

### The Lake House- 5 bedroom in quiet area with hot tub and pool table

8/10 Good

"House was very accommodating. We had a great time."

[](https://expedia.ca/Oakland-Hotels-The-Lake-House-5-Bedroom-In-Quiet-Area-With-Hot-Tub-And-Pool-Table.h120048180.Hotel-Information)

![Timroc II, FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!](https://images.trvl-media.com/lodging/24000000/23560000/23559700/23559605/w1199h798x1y1-5cea627c_y.jpg)

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

10/10 Excellent

"The host answered very quickly, the house was in perfect shape, we loved the hot tub and only about 15 minutes from wisp"

[](https://expedia.ca/Oakland-Hotels-Timroc-II.h23559605.Hotel-Information)

![Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing
](https://images.trvl-media.com/lodging/64000000/63750000/63746800/63746763/78c8b009_y.jpg)

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

10/10 Excellent

"The hosts were flexible and welcoming, it was great to know they were available to contact during the snow storm.:)"

[](https://expedia.ca/Oakland-Hotels-Lakefront.h63746763.Hotel-Information)

![Baja Motel](https://images.trvl-media.com/lodging/100000000/99840000/99839500/99839480/34bea603_y.jpg)

### Baja Motel

10/10 Excellent

"Clean, everything was great, nicely remodeled. Would stay again: "

[](https://expedia.ca/Oakland-Hotels-Riverside-Suites.h99839480.Hotel-Information)

![The Garrett Inn](https://images.trvl-media.com/lodging/15000000/14920000/14910400/14910340/d2b2d172_y.jpg)

### The Garrett Inn

10/10 Excellent

"Very kind staff, overall pleasant experience "

[](https://expedia.ca/Cumberland-Hotels-The-Garrett-Inn.h14910340.Hotel-Information)

![In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,](https://images.trvl-media.com/lodging/90000000/89150000/89146100/89146013/2fb0c438_y.jpg)

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

10/10 Excellent

"Host was great!! Got back to me right away when I had a question. We all had a great time! Great location!!"

[](https://expedia.ca/Oakland-Hotels-In-The-Heart-Of-Deep-Creek.h89146013.Hotel-Information)

![Level lakefront, family-friendly, hot tub, low fees, private dock](https://images.trvl-media.com/lodging/55000000/54920000/54911400/54911380/f7244719_y.jpg)

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

10/10 Excellent

"Cozy comfortable & clean house , super convenient to Wisp, yet private and quiet. "

[](https://expedia.ca/Cumberland-Hotels-Level-Lakefront.h54911380.Hotel-Information)

![Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip](https://images.trvl-media.com/lodging/96000000/95210000/95208700/95208674/7af77293_y.jpg)

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

10/10 Excellent

"This location was a great way for us to experience Deep Creek Lake in the winter months. The house was spacious, well-stocked, and spotless on arrival. We had a wonderful weekend and will look forward to coming back in the future!"

[](https://expedia.ca/Oakland-Hotels-Lakefront.h95208674.Hotel-Information)

![EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub](https://images.trvl-media.com/lodging/111000000/110100000/110092400/110092331/00441873_y.jpg)

### EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

10/10 Excellent

"This home was beautiful. The owners made sure we had everything we needed. Very beautiful and cozy!"

[](https://expedia.ca/Oakland-Hotels-EverGreenGrove-Hemlock2BR1-BADog-FriendlyHottub.h110092331.Hotel-Information)

## Find out more about Oakland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Oakland ](https://expedia.ca/Oakland-Private-Vacation-Homes.d9160-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cabin Rentals in Oakland ](https://expedia.ca/Oakland-Cabins.d9160-aaCabins.Travel-Guide-Accommodation)
- [Condo Rentals in Oakland ](https://expedia.ca/Oakland-Condos.d9160-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Oakland ](https://expedia.ca/Oakland-Apart-Hotels.d9160-aaApartHotels.Travel-Guide-Accommodation)
- [Cottages in Oakland ](https://expedia.ca/Oakland-Cottages.d9160-aaCottages.Travel-Guide-Accommodation)
- [Chalets in Oakland ](https://expedia.ca/Oakland-Chalets.d9160-aaChalets.Travel-Guide-Accommodation)
- [Apartments in Oakland ](https://expedia.ca/Oakland-Apartments.d9160-aaApartments.Travel-Guide-Accommodation)
- [Motels in Oakland ](https://expedia.ca/Oakland-Motels.d9160-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Oakland ](https://expedia.ca/Oakland-RV-Parks.d9160-aaRVParks.Travel-Guide-Accommodation)
- [Townhomes in Oakland ](https://expedia.ca/Oakland-Townhomes.d9160-aaTownhomes.Travel-Guide-Accommodation)

## Frequently asked questions

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