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The best vacation homes in Oakland

Check out our selection of great vacation homes in Oakland

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Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr, hotel in Oakland

Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr is a well-rounded recently renovated vacation home in Oakland.

Very close to great hiking trails. Beautiful house inside and out
Scored 10
10
Rated exceptional
Exceptional
10 reviews
Cubs Den - Hot Tub- Walk to Lake- Fire Pit - Kayaks, hotel in Oakland

This vacation home offers air-conditioned accommodations with a patio. With free Wifi, this 3-bedroom vacation home provides a TV and a kitchen with a dishwasher and oven.

Very clean and comfortable cabin. Close to everything. We’ll definitely be back next time we’re in town.
Scored 9.1
9.1
Rated wonderful
Wonderful
9 reviews
Oakland Retreat about 13 Mi to Deep Creek Lake!, hotel in Oakland

With free Wifi, this 3-bedroom vacation home provides a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and microwave.

A beautiful home which allowed us to truly relax and share w our family. So refreshing to not have to be concerned with other travelers.
Scored 9.4
9.4
Rated wonderful
Wonderful
5 reviews
Grandma's Cottage, hotel in Oakland

This pet-friendly vacation home also has free Wifi. The air-conditioned vacation home consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2...

It would have been great if we had been able to stay more than 2 days.
Scored 8.8
8.8
Rated excellent
Excellent
5 reviews
Woodsy Way Cabin, hotel in Oakland

This vacation home offers accommodations with a patio. This pet-friendly vacation home also has free Wifi.

The location was fabulous! The house was comfy.
Scored 8.2
8.2
Rated very good
Very Good
5 reviews
Birdhouse Lodge, hotel in Oakland

This pet-friendly vacation home also has free Wifi. The air-conditioned vacation home also features a TV, a fully equipped kitchen with an oven, a seating area, washing machine, and 2 bathrooms with a...

Location. Good WiFi. Nice neighborhood. Good response to my concerns by vacasa
Scored 7.2
7.2
Rated good
Good
12 reviews
Private Family Home with Deck, Porch and Forest Views!, hotel in Oakland

Featuring sea views, this vacation home also includes free Wifi. The air-conditioned vacation home consists of 3 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and a coffee...

Privacy
Scored 9.0
9.0
Rated wonderful
Wonderful
8 reviews
Still Meadows, hotel in Oakland

This pet-friendly vacation home also has free Wifi. Still Meadows features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with free toiletries.

Close to Shallow Falls and that there were a couple laundry pods available. We got wet from a hike and it was nice to not have to travel home with wet and dirty clothes
Scored 9.4
9.4
Rated wonderful
Wonderful
10 reviews
*Entire House • Sleeps 9 • Hot tub • Pets Welcome*, hotel in Oakland

*Entire House • Sleeps 9 • Hot tub • Pets Welcome* features a hot tub and free private parking, and is within 30 miles of Frostburg State University.

We LOVED everything about this place. It was Beautiful ....Comfortable....seriously very Homey. We had NO COMPLAINTS. Loved every minute of our stay. Hopefully we will be back next year.
Scored 9.5
9.5
Rated exceptional
Exceptional
12 reviews
Dancing Bear Lodge, hotel in Oakland

Both free Wifi and parking on-site are accessible at Dancing Bear Lodge free of charge.

The spacious open space. Allowing my mother who uses a walker to easily get around. I loved the porch with the rocking chairs and the patio outside was very nice.
Scored 9.2
9.2
Rated wonderful
Wonderful
5 reviews
All vacation homes in Oakland
Looking for a vacation home?
Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Oakland this month

Enjoy breakfast in Oakland!

  • Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 10 reviews

    Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr is a well-rounded recently renovated vacation home in Oakland.

    Very close to great hiking trails. Beautiful house inside and out

  • Cubs Den - Hot Tub- Walk to Lake- Fire Pit - Kayaks
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 9 reviews

    This vacation home offers air-conditioned accommodations with a patio. With free Wifi, this 3-bedroom vacation home provides a TV and a kitchen with a dishwasher and oven.

    It was peaceful and that was what we were after. Overall we were happy.

  • Oakland Retreat about 13 Mi to Deep Creek Lake!
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 5 reviews

    With free Wifi, this 3-bedroom vacation home provides a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and microwave.

  • Woodsy Way Cabin
    Breakfast options
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 5 reviews

    This vacation home offers accommodations with a patio. This pet-friendly vacation home also has free Wifi.

  • Grandma's Cottage
    Breakfast options
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 5 reviews

    This pet-friendly vacation home also has free Wifi. The air-conditioned vacation home consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2...

  • Mountain Laurel: New, Lake Access w. Dock Slip, Hot Tub, Dogs OK

    This vacation home features air-conditioned accommodations with a patio. The accommodation offers a 24-hour front desk and parking on-site.

  • Foxcroft: New, Lake Access w. Dock Slip, Hot Tub, Pool Table

    This vacation home provides air-conditioned accommodations with a patio. The accommodation offers a 24-hour front desk and parking on-site.

  • The Birdhouse
    Breakfast options

    Both free Wifi and parking on-site are available at The Birdhouse free of charge.

Save money on vacation homes in Oakland – budget options available!

  • Cabin Lodge
    Budget options available

    With free Wifi, this 5-bedroom vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and microwave. The accommodation has a fireplace.

  • 85 Hidden Cove Court
    Budget options available

    With free Wifi, this 6-bedroom vacation home features a TV and a kitchen with a dishwasher and microwave. The accommodation has a fireplace.

  • 3 Bears Lodge
    Budget options available

    Both free Wifi and parking on-site are accessible at 3 Bears Lodge free of charge.

  • Lakeland Views
    Budget options available

    Both free Wifi and parking on-site are accessible at Lakeland Views free of charge.

  • Sans Stress
    Budget options available

    There's a children's playground and guests have access to free Wifi and parking on-site.

  • Whispering Waters
    Budget options available

    Both parking on-site and free Wifi are accessible at Whispering Waters. Providing access to a patio with lake views, the spacious air-conditioned vacation home consists of 3 bedrooms.

  • Big Bass Lodge
    Budget options available
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 1 review

    Guests staying at this vacation home have access to a patio. Both parking on-site and free Wifi are available at Big Bass Lodge.

  • Big Boulder Retreat
    Budget options available

    Both parking on-site and free Wifi are accessible at Big Boulder Retreat.

Great access to the city center! Check these vacation homes in Oakland

  • 308D Two Bedroom Two Bath
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Offering a terrace, 308D Two Bedroom Two Bath offers accommodations in Oakland. This vacation home provides free private parking, a 24-hour front desk, and free Wifi.

  • 105A Efficiency One Bath
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Providing a terrace, 105A Efficiency One Bath offers accommodations in Oakland. This property offers access to a balcony, free private parking, and free Wifi.

  • Take-A-Break
    Central location
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Both free Wifi and parking on-site are available at Take-A-Break free of charge.

  • Heavenly Grove
    Central location
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Both free Wifi and parking on-site are accessible at Heavenly Grove free of charge.

  • The Haven
    Central location
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Both free Wifi and parking on-site are accessible at The Haven free of charge.

  • 306C One Bedroom One Bath
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 2 reviews

    Providing a terrace, 306C One Bedroom One Bath provides accommodations in Oakland. This vacation home offers free private parking, a 24-hour front desk, and free Wifi.

  • Home Sweet Cabin
    Central location
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 2 reviews

    Both free Wifi and parking on-site are accessible at Home Sweet Cabin free of charge.

  • Bear Necessities @ Deep Creek Lake
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 4 reviews

    The property provides free private parking. The air-conditioned vacation home is composed of 1 separate bedroom, a living room, a fully equipped kitchen with an oven and microwave, and 1 bathroom.

  • 103A Efficiency One Bath
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 3 reviews

    Providing a terrace, 103A Efficiency One Bath features accommodations in Oakland. This property offers access to a balcony, free private parking, and free Wifi.

  • 204B One Bedroom One Bath
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 2 reviews

    Offering a terrace, 204B One Bedroom One Bath offers accommodations in Oakland. This vacation home provides free private parking, a 24-hour front desk, and free Wifi.

  • 309B One Bedroom One Bath
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 1 review

    Featuring a terrace, 309B One Bedroom One Bath features accommodations in Oakland. This vacation home provides free private parking, a 24-hour front desk, and free Wifi.

  • 205A Efficiency One Bath
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 1 review

    Featuring a terrace, 205A Efficiency One Bath provides accommodations in Oakland. This property offers access to a balcony, free private parking, and free Wifi.

  • Oakland Vacation Rental Less Than 1 Mi to Deep Creek Lake!
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 1 review

    With free Wifi, this 2-bedroom vacation home features a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the vacation home.

  • 307C One Bedroom One Bath
    Scored 7.5
    7.5
    Rated good
    Good
     · 2 reviews

    Featuring a terrace, 307C One Bedroom One Bath features accommodations in Oakland. This vacation home offers free private parking, a 24-hour front desk, and free Wifi.

  • 706H Studio Loft One Bath
    Scored 6.0
    6.0
    Rated pleasant
    Pleasant
     · 4 reviews

    Featuring a terrace, 706H Studio Loft One Bath provides accommodations in Oakland. This property offers access to a balcony, free private parking, and free Wifi.

  • Lake House
    Central location
    Scored 5.0
    5.0
    Rated fair
    Average
     · 1 review

    Both free Wifi and parking on-site are available at Lake House free of charge.

  • 304C One Bedroom One Bath
    Scored 4.0
    4.0
    Rated disappointing
    Disappointing
     · 1 review

    Offering a terrace, 304C One Bedroom One Bath offers accommodations in Oakland. This vacation home features free private parking, a 24-hour front desk, and free Wifi.

  • Unreel
    Central location
    Scored 4.0
    4.0
    Rated disappointing
    Disappointing
     · 1 review

    Both free Wifi and parking on-site are available at Unreel free of charge.

  • Yes Deer
    Central location
    Scored 3.0
    3.0
    Rated poor
    Poor
     · 1 review

    Both free Wifi and parking on-site are accessible at Yes Deer free of charge.

  • 708H Studio Loft One Bath

    Featuring a terrace, 708H Studio Loft One Bath provides accommodations in Oakland. This property offers access to a balcony, free private parking, and free Wifi.

  • 512G Two Bedroom One Bath

    Offering a terrace, 512G Two Bedroom One Bath offers accommodations in Oakland. This vacation home provides free private parking, a 24-hour front desk, and free Wifi.

  • 507G Two Bedroom One Bath

    Offering a terrace, 507G Two Bedroom One Bath offers accommodations in Oakland. This vacation home provides free private parking, a 24-hour front desk, and free Wifi.

  • 504F Three Bedroom Two Bath

    Offering a terrace, 504F Three Bedroom Two Bath offers accommodations in Oakland. This vacation home provides free private parking, a 24-hour front desk, and free Wifi.

  • 503F Three Bedroom Two Bath

    Offering a terrace, 503F Three Bedroom Two Bath offers accommodations in Oakland. This vacation home features free private parking, a 24-hour front desk, and free Wifi.

  • 502F Three Bedroom Two Bath

    Featuring a terrace, 502F Three Bedroom Two Bath features accommodations in Oakland. This vacation home offers free private parking, a 24-hour front desk, and free Wifi.

  • 305E Three Bedroom Three Bath

    Providing a terrace, 305E Three Bedroom Three Bath provides accommodations in Oakland. This vacation home offers free private parking, a 24-hour front desk, and free Wifi.

  • 303D Two Bedroom Two Bath

    Providing a terrace, 303D Two Bedroom Two Bath provides accommodations in Oakland. This vacation home features free private parking, a 24-hour front desk, and free Wifi.

  • 301D Two Bedroom Two Bath

    Offering a terrace, 301D Two Bedroom Two Bath offers accommodations in Oakland. This vacation home provides free private parking, a 24-hour front desk, and free Wifi.

FAQ about vacation homes in Oakland

Vacation Homes That Guests Love in Oakland

  • Avg. price/night: $123.12
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 182 reviews
    Location was great, room was very clean.
    C
    Claudia
    Family with young children
  • Avg. price/night: $117.99
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 309 reviews
    The location is great. Very clean , very comfortable and friendly staff
    Duling
    Young couple
  • Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 161 reviews
    Location good…very clean…bed comfortable. Bed linens nice
    cooper
    Family with young children
  • Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 161 reviews
    Everything about the Long Branch was wonderful. Very clean and new. The staff was exceptional as well. This is our second stay with them. We loved our first stay just as much as our second. We will be back.
    J
    Judy
    Young couple
  • Scored 8.5
    8.5
    Rated very good
    Very Good
     · 147 reviews
    location was great. very clean and quiet. would stay here again.
    roger
    Young couple
  • Avg. price/night: $119.70
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 138 reviews
    The room was very, very clean. It also seemed newly renovated. There wasn’t even any dust anywhere.
    Scott
    Young couple