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Compare 498 Vacation Homes in Oakland with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (16)
"The house was beautiful and clean and in a great location (and smelled great too!). We arrived on Thanksgiving day and were pleasantly surprised to find a decorated Christmas tree lit by the fireplace. The house is a very convenient 10-15 minute drive to Oakland or McHenry. We loved sitting in the hot tub while it was snowing. Our granddaughter enjoyed the arcade game upstairs and was really excited about the bunk bed room. We had a wonderful stay and would love to come back in the warmer...
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Serene Mountain Escape: Hot Tub, Foosball, Views

9.4 out of 10, Exceptional, (3)
"House was very clean and well appointed. Nice location"
Serene Mountain Escape: Hot Tub, Foosball, Views

Lakefront/Dock/Amazing views HotTub

9.8 out of 10, Exceptional, (40)
"Great central location right off busy Garrett Highway. Nice amenities, could even suit 3 distinct groups with sleeping for 14. Walk out lower level directly to the lake, steps away. Nice hot tub, dock and kayaks. Fun game table and some arcade games if children come along. Enjoyable evening by the fire pit with s'mores! Easy to find, easy to book, responsive owners."
Lakefront/Dock/Amazing views HotTub

Lakefront, dog friendly, dock slip, hot tub, and fire pit

10.0 out of 10, Exceptional, (32)
"Our family enjoys DCL every other year for Thanksgiving. This year, we stayed at Magnolia and we were not disappointed. The house was well stocked with every-thing we needed. We loved the different sitting arrangements that afforded all of us a place to escape from the chaos, when necessary. "
Lakefront, dog friendly, dock slip, hot tub, and fire pit

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

10.0 out of 10, Exceptional, (95)
"Enjoyed the house love you Can see the lake from "
Level lakefront, family-friendly, hot tub, low fees, private dock

Modern house on the lake with private dock, hot tub, air hockey & central AC

7.6 out of 10, Good, (16)
"Nice spot. A little loud with the highway and would have liked to have been able to use hottub but it didnt look clean. Otherwise great spot, super convenient for popping around the lake area."
Modern house on the lake with private dock, hot tub, air hockey & central AC

Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

9.6 out of 10, Exceptional, (76)
"Great place and close to Wisp. Really enjoyed our stay! Will book there again. Great location with fire pit and yard! Just one small issue - there were dozens of lady bugs in the upstairs bedroom. It was fine but thought you all should know."
Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

Private Lodge sleeps 25 guests Spectacular Views

The price is SAR 2,141
SAR 2,567 total
includes taxes & fees
5 Jan - 6 January 2025
Private Lodge sleeps 25 guests Spectacular Views

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

8.8 out of 10, Excellent, (39)
"Everything was just as described. Very clean and in a great location! Owner was so easy to work with. I would definitely book again! "
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Amazing Central Location! Lakefront! Hot tub/dock!

9.4 out of 10, Exceptional, (43)
"Plenty of room for our large group and the house is in great condition. Checking in and out was simple, and the hosts were very responsive to questions before our stay."
Amazing Central Location! Lakefront! Hot tub/dock!

New! Serenity Shores: Lake Area, Dogs OK, Hot Tub, Fireplace, Fire Pit, A/C!

9.2 out of 10, Wonderful, (16)
"We love the fire pit making s’mores with family and friends! Loved the hot tub! Very quiet wooded area, saw a black bear at the end of the property! We loved our stay! "
New! Serenity Shores: Lake Area, Dogs OK, Hot Tub, Fireplace, Fire Pit, A/C!

Dog-friendly house on the lake, central AC, & EV charger

8.6 out of 10, Excellent, (48)
"My sister, daughter and I were in wow mode from the moment we walked in the door. The pictures on line did not do justice to the "Million Dollar View" description. The place was very clean, inviting, accommodating and beautiful! Appliances were very updated and snacks and treats were also left on the counter for us. Owner thought of everything to make this as pleasant as it was for us. We will definitely return again. Thank you"
Dog-friendly house on the lake, central AC, & EV charger

Deep Creek Lake Townhome w/ Deck & Water Views

9.6 out of 10, Exceptional, (32)
"Very clean and well maintained. Decor includes interesting items from around the world. Master bed was comfy, and owner was friendly on the phone. When she learned we were coming for my husband's birthday, she left a fun card for him with all the check-in info. We went in October and enjoyed the cozy gas fireplace and beautiful lake view. A busy road stands between the condo and the lake, but it's not a huge issue in cold weather when windows are closed. If you're looking for remote mountain...
Deep Creek Lake Townhome w/ Deck & Water Views

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

8.8 out of 10, Excellent, (8)
"We had a great long weekend staying at The Rusty Nail! This house has literally everything you need inside. We enjoyed all the amenities such as the hot tub, sauna, shuffleboard and basketball hoop in the basement. The large common areas made it easy to all visit and be together. The bedroom arrangements were great and everyone had a comfortable place to sleep. The home looked like it was just recently painted outside and it looks great! The location is private but also so close to everything....
5BR lakefront retreat with hot tub, sauna, & dock

Summerside: Lakefront, Dock Slip, Hot Tub, Fire Pit, Pool Table!

9.0 out of 10, Wonderful, (14)
"The property was amazing! We loved the home and the surroundings. We would definitely book this home again. Due to well issues we had to move. The home we had to move to was also beautiful but not the location we were looking for. We have not yet been appropriately accommodated for our forced move and the resulting loss of boat time, move, investment."
Summerside: Lakefront, Dock Slip, Hot Tub, Fire Pit, Pool Table!

New! Red Cottage: Split Lake Front, Dogs Welcome, Dock Slip, Hot Tub!

9.6 out of 10, Exceptional, (17)
"This cottage has lovely views of the lake. The highway traffic noise is a bit loud. We knew both those things before renting. The kitchen was small but very practical. The beds were comfy."
New! Red Cottage: Split Lake Front, Dogs Welcome, Dock Slip, Hot Tub!

Indoor Pool, Huge Home, Best View of the Lake!

9.0 out of 10, Wonderful, (39)
"Deep Creek Lake, and this house, proved to be the perfect find for our family reunion. From variety of outdoor activities for different ages to bedroom layout and bonus features, it was clear everyone had a great time. The house is aging and has a few maintenance issues that need to be addressed by the owners, but the property management’s communications with us were among the best I’ve experienced among VRBO and similar services. I had complete confidence that if the gas grill’s propane tank...
Indoor Pool, Huge Home, Best View of the Lake!

Blue Sky Lodge: Lake Access, Hot Tub, Pool table, 2 Fire Pits, Grill!

9.4 out of 10, Exceptional, (44)
"We stayed here for a long weekend with friends and family. The layout of the home was especially accommodating for each of the families staying with us and the location was great. I would only caution that the home is located on a steep slope and the walk down the drive to the front door might be a problem if the party were to include someone that had difficulty with that sort of thing. For us, thiugh, it was wonderful!"
Blue Sky Lodge: Lake Access, Hot Tub, Pool table, 2 Fire Pits, Grill!

Absolute Delight: Lakefront, Hot Tub, Dock Slip, Pool Table, Deck!

9.4 out of 10, Exceptional, (11)
"This house was an excellent place for our co bach trip enough space for everyone to be comfortable a great place for quiet and beautiful views. House was very clean and very well stock of kitchen supply. Couple tvs didn’t work and for check in our code didn’t work but it was fixed fast. Had a great weekend! "
Absolute Delight: Lakefront, Hot Tub, Dock Slip, Pool Table, Deck!

LakeAccess 4BR DeckSlide OD Movies HotTub Kayaks

9.8 out of 10, Exceptional, (7)
"This house is lovely and is wonderful for families. We are three generations. The children loved the slide. All of us enjoyed making S’mores in the fire pit, relaxing in the hot tub and watching movies on the deck in the evening with some popcorn. Also, the house was very clean which is important to us. This all made for a nice vacation."
LakeAccess 4BR DeckSlide OD Movies HotTub Kayaks
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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Other property types in Oakland

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

10.0 out of 10, Exceptional, (16)
"The house was beautiful and clean and in a great location (and smelled great too!). We arrived on Thanksgiving day and were pleasantly surprised to find a decorated Christmas tree lit by the fireplace. The house is a very convenient 10-15 minute drive to Oakland or McHenry. We loved sitting in the hot tub while it was snowing. Our granddaughter enjoyed the arcade game upstairs and was really excited about the bunk bed room. We had a wonderful stay and would love to come back in the warmer...
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Dog-friendly cabin with private hot tub, Ping-Pong & lake views

8.6 out of 10, Excellent, (77)
"A beautifully furnished cabin so close to the amenities and state parks of Deep Creek Lake. So well stocked with everything you need "
Dog-friendly cabin with private hot tub, Ping-Pong & lake views

Modern house on the lake with private dock, hot tub, air hockey & central AC

7.6 out of 10, Good, (16)
"Nice spot. A little loud with the highway and would have liked to have been able to use hottub but it didnt look clean. Otherwise great spot, super convenient for popping around the lake area."
Modern house on the lake with private dock, hot tub, air hockey & central AC
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.