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Search Vacation Homes in Oakland

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Browse Select Oakland Vacation Homes

Cross the River
3.5 out of 5
74 Riverview Terrace, Oakland, MD, 21550
Cross the River
Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!
3.9/5 Good! (7 reviews)
Truly Amazing!
"We had a fantastic time at the Herrington Manor House. This lovely house had great amenities, indoor and outdoor. Very spacious well decorated rooms, beautifully well kept grounds. Our family enjoy every moment of our time there, we’ll definitely be back."

Reviewed on Aug 17, 2021

Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!
Lakefront Home w/Private Indoor Pool, Private Dock, & Hot Tub!
3.7/5 Good! (3 reviews)
60th
"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 ..."

Reviewed on Oct 3, 2020

Lakefront Home w/Private Indoor Pool, Private Dock, & Hot Tub!
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Conveniently located log cabin with outdoor hot tub!
4.3/5 Excellent! (3 reviews)
Our Next get away!
"⭐⭐⭐⭐⭐"

Reviewed on Jan 19, 2022

Conveniently located log cabin with outdoor hot tub!
Celebration at Deep Creek 8 Bedroom House
Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK
4.7/5 Exceptional! (15 reviews)
Great location!
"Long weekend getaway with family. Wonderful location. Close to Wisp ski resort, restaurants, market and to deep creek lake state park. Had a great time!"

Reviewed on Mar 21, 2022

Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK
NEW! Peaceful Townhome < 1 Mi to Deep Creek Lake!
5/5 Exceptional! (2 reviews)
Winter wonderland
"Thank you for hosting our winter wonderland stay in Deep Creek Lake. We will return!"

Reviewed on Jan 25, 2022

NEW! Peaceful Townhome < 1 Mi to Deep Creek Lake!
A310- Standard view studio & loft, sleeps 6, cozy fireplace & free wifi!
The Haven 8 Bedroom House
4 out of 5
1131 Lake Shore Drive, Oakland, MD, 21550
The Haven 8 Bedroom House
Sunset Delight 9 Bedroom House
3.5 out of 5
25 Old Chestnut Drive, Oakland, MD, 21550
Sunset Delight 9 Bedroom House
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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.

Other property types in Oakland

Cozy condo w/spectacular lake view, deck & fireplace - close to lake activities!
4.3/5 Excellent! (7 reviews)
Very nice
"Beautiful little quaint place that is close to everything you want to do. We loved it. Very clean and had everything we needed."

Reviewed on Mar 2, 2022

Cozy condo w/spectacular lake view, deck & fireplace - close to lake activities!
Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!
3.9/5 Good! (7 reviews)
Truly Amazing!
"We had a fantastic time at the Herrington Manor House. This lovely house had great amenities, indoor and outdoor. Very spacious well decorated rooms, beautifully well kept grounds. Our family enjoy every moment of our time there, we’ll definitely be back."

Reviewed on Aug 17, 2021

Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!
Wooded Lake Area Cabin w/Hot Tub, Wood Fireplace, & Shuffleboard!
4.7/5 Exceptional! (14 reviews)
"Gorgeous space. Perfect for a quick romantic or family getaway. We LOVED everything about it except that there were no stairs or handrail for getting into the hottub which we thought was a safety issue. The wifi was strong and reliable. The TV was big! The beautiful wooden walls and ceilings were ..."

Reviewed on Dec 10, 2021

Wooded Lake Area Cabin w/Hot Tub, Wood Fireplace, & Shuffleboard!
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.

Recent Reviews in Oakland
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