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Browse Select Oakland Vacation Homes

Cross the River

Cross the River
3.5 out of 5
74 Riverview Terrace, Oakland, MD, 21550
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Cross the River
Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!

Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!
Oakland, MD
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

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Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!
Lakefront Home w/Private Indoor Pool, Private Dock, & Hot Tub!

Lakefront Home w/Private Indoor Pool, Private Dock, & Hot Tub!
Oakland, MD
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

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Lakefront Home w/Private Indoor Pool, Private Dock, & Hot Tub!
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Conveniently located log cabin with outdoor hot tub!

Conveniently located log cabin with outdoor hot tub!
Oakland, MD
4.3/5 Excellent! (3 reviews)
Our Next get away!
"⭐⭐⭐⭐⭐"

Reviewed on Jan 19, 2022

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Conveniently located log cabin with outdoor hot tub!
Celebration at Deep Creek 8 Bedroom House

Celebration at Deep Creek 8 Bedroom House
4 out of 5
179 Glendale Rd., Oakland, MD, 21550
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Celebration at Deep Creek 8 Bedroom House
Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK

Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK
Oakland, MD
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

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Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK
NEW! Peaceful Townhome < 1 Mi to Deep Creek Lake!

NEW! Peaceful Townhome < 1 Mi to Deep Creek Lake!
Oakland, MD
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

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NEW! Peaceful Townhome < 1 Mi to Deep Creek Lake!
A310- Standard view studio & loft, sleeps 6, cozy fireplace & free wifi!

A310- Standard view studio & loft, sleeps 6, cozy fireplace & free wifi!
Oakland, MD
The price is $114 per night from May 22 to May 23
A310- Standard view studio & loft, sleeps 6, cozy fireplace & free wifi!
The Haven 8 Bedroom House

The Haven 8 Bedroom House
4 out of 5
1131 Lake Shore Drive, Oakland, MD, 21550
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The Haven 8 Bedroom House
Sunset Delight 9 Bedroom House

Sunset Delight 9 Bedroom House
3.5 out of 5
25 Old Chestnut Drive, Oakland, MD, 21550
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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!

Cozy condo w/spectacular lake view, deck & fireplace - close to lake activities!
Oakland, MD
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!

Largest Rental Estate in MD! Private Indoor Pool, Home Theater, & 3 Hot Tubs!
Oakland, MD
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!

Wooded Lake Area Cabin w/Hot Tub, Wood Fireplace, & Shuffleboard!
Oakland, MD
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
expedia verified reviews

  • Inn At Deep Creek

    Inn At Deep Creek

    5/5 Excellent
    "Nice size rooms with kitchen and living area."
    A verified traveler from Gettysburg stayed at Inn At Deep Creek
    Posted 3 days ago
    Inn At Deep Creek
  • Oak Mar Motel

    Oak Mar Motel

    5/5 Excellent
    " Great service. The manager/owner was super nice. The food at the diner was delicious. Will definitely stay there again."
    A verified traveler stayed at Oak Mar Motel
    Posted 2 weeks ago
    Oak Mar Motel
  • The Garrett Inn

    The Garrett Inn

    5/5 Excellent
    "A nice inn."
    A verified traveler stayed at The Garrett Inn
    Posted 3 weeks ago
    The Garrett Inn
  • Lovin Life Deep Creek 5 STAR -5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub

    Lovin Life Deep Creek 5 STAR -5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub

    5/5 Excellent
    Great house for girl’s weekend! Comfortable, spacious and great location.
    "The owners were responsive and helpful! Great experience."
    A verified traveler stayed at Lovin Life Deep Creek 5 STAR -5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub
    Posted 1 month ago
    Lovin Life Deep Creek 5 STAR -5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub
  • Cozy Cabin w/Indoor Hot Tub, 2 Wood Fireplaces, & Foosball Table!

    Cozy Cabin w/Indoor Hot Tub, 2 Wood Fireplaces, & Foosball Table!

    5/5 Excellent
    Relaxing Cabin Getaway
    "Everything was exactly as described. Very clean and had everything we needed. We loved the hot tub. Lots of games to play as well. We'll be back for sure."
    A verified traveler stayed at Cozy Cabin w/Indoor Hot Tub, 2 Wood Fireplaces, & Foosball Table!
    Posted 2 months ago
    Cozy Cabin w/Indoor Hot Tub, 2 Wood Fireplaces, & Foosball Table!
  • MoonWinks...w/LakeView and Close to All Activities

    MoonWinks...w/LakeView and Close to All Activities

    5/5 Excellent
    Had a very enjoyable stay.
    "Just right for our needs for our weekend stay."
    A verified traveler stayed at MoonWinks...w/LakeView and Close to All Activities
    Posted 3 months ago
    MoonWinks...w/LakeView and Close to All Activities
  • Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!

    Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!

    3/5 Okay
    Girls Weekend
    "It was fine but just a couple of things. Couldn’t really use the hot tub on Friday when we arrived. They came to test the chemicals and recommended it be drained. I feel like this should have been done before we arrived. It was cold, not enough heating baseboard units. Power went out and the cable didn’t work because the remotes were the wrong ones and batteries were missing."
    A verified traveler stayed at Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!
    Posted 3 months ago
    Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!
  • Cozy condo w/spectacular lake view, deck & fireplace - close to lake activities!

    Cozy condo w/spectacular lake view, deck & fireplace - close to lake activities!

    5/5 Excellent
    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."
    A verified traveler stayed at Cozy condo w/spectacular lake view, deck & fireplace - close to lake activities!
    Posted 3 months ago
    Cozy condo w/spectacular lake view, deck & fireplace - close to lake activities!
  • Conveniently located log cabin with outdoor hot tub!

    Conveniently located log cabin with outdoor hot tub!

    5/5 Excellent
    Our Next get away!
    "⭐⭐⭐⭐⭐"
    A verified traveler stayed at Conveniently located log cabin with outdoor hot tub!
    Posted 4 months ago
    Conveniently located log cabin with outdoor hot tub!

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