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The best holiday homes in Oakland

Check out our pick of great holiday 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 recently renovated holiday home in Oakland, where guests can make the most of its spa and wellness centre and open-air bath.

Everything was perfect. The cabin has everything, you just need to bring you clothes and that it it. I really recommend staying more than two days to get all the experience.
Scored 10
10
Rated exceptional
Exceptional
10 reviews
Cubs Den - Hot Tub- Walk to Lake- Fire Pit - Kayaks, hotel in Oakland

Featuring air-conditioned accommodation with a patio, Cubs Den - Hot Tub- Walk to Lake- Fire Pit - Kayaks is located in Oakland.

Scored 9.1
9.1
Rated superb
Superb
9 reviews
Oakland Retreat about 13 Mi to Deep Creek Lake!, hotel in Oakland

Featuring a spa bath, Oakland Retreat about 13 Mi to Deep Creek Lake! is located in Oakland. Free WiFi is available throughout the property.

Scored 9.4
9.4
Rated superb
Superb
5 reviews
Grandma's Cottage, hotel in Oakland

Grandma's Cottage is situated in Oakland. Free WiFi is provided throughout the property.

Scored 8.8
8.8
Rated fabulous
Fabulous
5 reviews
Woodsy Way Cabin, hotel in Oakland

Set in Oakland in the Maryland region, Woodsy Way Cabin features a patio. Free WiFi is included throughout the property.

Scored 8.2
8.2
Rated very good
Very good
5 reviews
Birdhouse Lodge, hotel in Oakland

Birdhouse Lodge is situated in Oakland. Free WiFi is at guests' disposal throughout the property.

No breakfast was their
Scored 7.2
7.2
Rated good
Good
12 reviews
Private Family Home with Deck, Porch and Forest Views!, hotel in Oakland

Boasting a spa bath, Private Family Home with Deck, Porch and Forest Views! is situated in McComas Beach. Free WiFi is provided throughout the property.

Scored 9.0
9.0
Rated superb
Superb
8 reviews
Still Meadows, hotel in Oakland

Still Meadows is situated in McComas Beach. Free WiFi is at guests' disposal throughout the property.

Scored 9.4
9.4
Rated superb
Superb
10 reviews
*Entire House • Sleeps 9 • Hot tub • Pets Welcome*, hotel in Oakland

Located in McHenry, within 48 km of Frostburg State University, *Entire House • Sleeps 9 • Hot tub • Pets Welcome* offers accommodation with air conditioning. A hot tub is available for guests.

Scored 9.5
9.5
Rated exceptional
Exceptional
12 reviews
Dancing Bear Lodge, hotel in Oakland

Dancing Bear Lodge is situated in McHenry. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

Scored 9.2
9.2
Rated superb
Superb
5 reviews
All holiday homes in Oakland
Looking for a holiday home?
Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday 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 recently renovated holiday home in Oakland, where guests can make the most of its spa and wellness centre and open-air bath.

    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 superb
    Superb
     · 9 reviews

    Featuring air-conditioned accommodation with a patio, Cubs Den - Hot Tub- Walk to Lake- Fire Pit - Kayaks is located in Oakland.

    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 superb
    Superb
     · 5 reviews

    Featuring a spa bath, Oakland Retreat about 13 Mi to Deep Creek Lake! is located in Oakland. Free WiFi is available throughout the property.

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

    Set in Oakland in the Maryland region, Woodsy Way Cabin features a patio. Free WiFi is included throughout the property.

  • Grandma's Cottage
    Breakfast options
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 5 reviews

    Grandma's Cottage is situated in Oakland. Free WiFi is provided throughout the property.

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

    Featuring air-conditioned accommodation with a patio, Mountain Laurel: New, Lake Access w. Dock Slip, Hot Tub, Dogs OK is located in Oakland.

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

    Boasting air-conditioned accommodation with a patio, Foxcroft: New, Lake Access w. Dock Slip, Hot Tub, Pool Table is situated in Oakland.

  • The Birdhouse
    Breakfast options

    The Birdhouse is located in Oakland. Both free WiFi and parking on-site are available at the holiday home free of charge.

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

  • Cabin Lodge
    Budget options available

    Cabin Lodge is situated in Oakland. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • 85 Hidden Cove Court
    Budget options available

    85 Hidden Cove Court is situated in Oakland. The property has lake views. With free WiFi, this 6-bedroom holiday home features a TV and a kitchen with a dishwasher and microwave.

  • 3 Bears Lodge
    Budget options available

    3 Bears Lodge is situated in Oakland. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Lakeland Views
    Budget options available

    Lakeland Views is set in Oakland. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Sans Stress
    Budget options available

    Boasting a hot tub, Sans Stress is situated in Oakland. Free WiFi is provided throughout the property.

  • Whispering Waters
    Budget options available

    Situated in Oakland, Whispering Waters features air-conditioned accommodation with a patio and free WiFi. The property has lake views.

  • Big Bass Lodge
    Budget options available
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1 review

    Set in Oakland in the Maryland region, Big Bass Lodge features a patio. Free WiFi is included throughout the property.

  • Big Boulder Retreat
    Budget options available

    Big Boulder Retreat is set in Oakland. Free WiFi is at guests' disposal throughout the property.

Great access to the city centre! Check these holiday homes in Oakland

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

    308D Two Bedroom Two Bath is located in Oakland and offers a terrace. This holiday 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 accommodation in Oakland. This holiday home provides free private parking, a 24-hour front desk and free WiFi.

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

    Take-A-Break is set in Oakland. Both free WiFi and parking on-site are available at the holiday home free of charge.

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

    Boasting a spa bath, Heavenly Grove is situated in Oakland. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

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

    Boasting air-conditioned accommodation with a private pool, The Haven is situated in Oakland. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

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

    306C One Bedroom One Bath is set in Oakland and offers a terrace. This holiday home offers free private parking, a 24-hour front desk and free WiFi.

  • Home Sweet Cabin
    Central location
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 2 reviews

    Boasting a spa bath, Home Sweet Cabin is set in Oakland. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Bear Necessities @ Deep Creek Lake
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 4 reviews

    Located in Oakland in the Maryland region, Bear Necessities @ Deep Creek Lake provides accommodation with free private parking.

  • 103A Efficiency One Bath
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 3 reviews

    Providing a terrace, 103A Efficiency One Bath features accommodation in Oakland. This holiday home provides free private parking, a 24-hour front desk and free WiFi.

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

    Providing a terrace, 204B One Bedroom One Bath offers accommodation in Oakland. This holiday 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

    309B One Bedroom One Bath is located in Oakland and offers a terrace. This holiday 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 accommodation in Oakland. This holiday home features free private parking, a 24-hour front desk 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

    Oakland Vacation Rental Less Than 1 Mi to Deep Creek Lake! is situated in Oakland. Free WiFi is at guests' disposal throughout the property.

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

    Offering a terrace, 307C One Bedroom One Bath features accommodation in Oakland. This holiday 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 accommodation in Oakland. This holiday home features free private parking, a 24-hour front desk and free WiFi.

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

    Featuring a spa bath, Lake House is located in Oakland. Both free WiFi and parking on-site are available at the holiday home free of charge.

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

    304C One Bedroom One Bath is situated in Oakland and offers a terrace. This holiday 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

    Unreel is set in Oakland. Both free WiFi and parking on-site are available at the holiday home free of charge.

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

    Yes Deer is situated in Oakland. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • 708H Studio Loft One Bath

    Featuring a terrace, 708H Studio Loft One Bath provides accommodation in Oakland. This holiday home features free private parking, a 24-hour front desk and free WiFi.

  • 512G Two Bedroom One Bath

    512G Two Bedroom One Bath is located in Oakland and offers a terrace. This holiday home provides free private parking, a 24-hour front desk and free WiFi.

  • 507G Two Bedroom One Bath

    Providing a terrace, 507G Two Bedroom One Bath offers accommodation in Oakland. This holiday home provides free private parking, a 24-hour front desk and free WiFi.

  • 504F Three Bedroom Two Bath

    Providing a terrace, 504F Three Bedroom Two Bath offers accommodation in Oakland. This holiday home provides free private parking, a 24-hour front desk and free WiFi.

  • 503F Three Bedroom Two Bath

    503F Three Bedroom Two Bath is situated in Oakland and offers a terrace. This holiday home features free private parking, a 24-hour front desk and free WiFi.

  • 502F Three Bedroom Two Bath

    Offering a terrace, 502F Three Bedroom Two Bath features accommodation in Oakland. This holiday home offers free private parking, a 24-hour front desk and free WiFi.

  • 305E Three Bedroom Three Bath

    Offering a terrace, 305E Three Bedroom Three Bath provides accommodation in Oakland. This holiday home offers free private parking, a 24-hour front desk and free WiFi.

  • 303D Two Bedroom Two Bath

    303D Two Bedroom Two Bath is situated in Oakland and offers a terrace. This holiday home features free private parking, a 24-hour front desk and free WiFi.

  • 301D Two Bedroom Two Bath

    Providing a terrace, 301D Two Bedroom Two Bath offers accommodation in Oakland. This holiday home provides free private parking, a 24-hour front desk and free WiFi.

FAQ about holiday homes in Oakland

Holiday homes that guests love in Oakland

  • Avg. price/night: £97.49
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 182 reviews
    Location was great, room was very clean.
    C
    Claudia
    Family with young children
  • Avg. price/night: £93.43
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 309 reviews
    The location is great. Very clean , very comfortable and friendly staff
    Duling
    Young couple
  • Scored 9.3
    9.3
    Rated superb
    Superb
     · 161 reviews
    Location good…very clean…bed comfortable. Bed linens nice
    cooper
    Family with young children
  • Scored 9.3
    9.3
    Rated superb
    Superb
     · 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: £94.78
    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