Beginning of main content

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any vacation rental reservation


Vacation Rentals in Oakland

See all Vacation Rentals in Oakland
Artic Retreat is one Tranquil Oasis! Embrace the Wild and Restless Energy of This Wooded Retreat!

Artic Retreat is one Tranquil Oasis! Embrace the Wild and Restless Energy of This Wooded Retreat!

, OAKLAND
     
     

    Situated in a rural location, this romantic vacation home is 2.3 mi (3.7 km) from Deep Creek Lake State Park and within 9 mi (15 km) of Wisp Resort and Thousand ...

    Artic Retreat is one Tranquil Oasis! Embrace the Wild and Restless Energy of This Wooded Retreat!Get Rates

    Artic Retreat is one Tranquil Oasis! Embrace the Wild and Restless Energy of This Wooded Retreat!Get Rates
    Rustic and Warm, Bunbury Cottage is a Charming Lincoln-lodge Style Home With Lots to Offer!

    Rustic and Warm, Bunbury Cottage is a Charming Lincoln-lodge Style Home With Lots to Offer!

    , OAKLAND
       
       

      Situated in a rural location, this romantic vacation home is 6 mi (9.6 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Cranesville ...

      Rustic and Warm, Bunbury Cottage is a Charming Lincoln-lodge Style Home With Lots to Offer!Get Rates

      Rustic and Warm, Bunbury Cottage is a Charming Lincoln-lodge Style Home With Lots to Offer!Get Rates
      Walk to the Waterfalls and Explore the Winding Trails Around Swallow Falls Inn Cabin 2!

      Walk to the Waterfalls and Explore the Winding Trails Around Swallow Falls Inn Cabin 2!

      , OAKLAND
         
         

        Situated in a rural location, this romantic vacation home is within 9 mi (15 km) of Cranesville Swamp Natural Area, Wisp Resort, and Deep Creek Lake State Park. ...

        Walk to the Waterfalls and Explore the Winding Trails Around Swallow Falls Inn Cabin 2!Get Rates

        Walk to the Waterfalls and Explore the Winding Trails Around Swallow Falls Inn Cabin 2!Get Rates
        Intimate and Inviting, Swallow Falls Inn Cabin 1 Echoes With the Wild Resonance of the Waterfalls!

        Intimate and Inviting, Swallow Falls Inn Cabin 1 Echoes With the Wild Resonance of the Waterfalls!

        , OAKLAND
           
           
          4.8 out of 5 (4 reviews)

          Situated in a rural location, this romantic vacation home is within 9 mi (15 km) of Cranesville Swamp Natural Area, Wisp Resort, and Deep Creek Lake State Park. ...

          Intimate and Inviting, Swallow Falls Inn Cabin 1 Echoes With the Wild Resonance of the Waterfalls!Get Rates

          Intimate and Inviting, Swallow Falls Inn Cabin 1 Echoes With the Wild Resonance of the Waterfalls!Get Rates
          Home on the Ridge is a Sweet and Spacious Dwelling With Breathtaking Mountain-lake Views!

          Home on the Ridge is a Sweet and Spacious Dwelling With Breathtaking Mountain-lake Views!

          , OAKLAND
             
             

            Situated in a rural location, this romantic vacation home is 4.3 mi (7 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Thousand ...

            Home on the Ridge is a Sweet and Spacious Dwelling With Breathtaking Mountain-lake Views!Get Rates

            Home on the Ridge is a Sweet and Spacious Dwelling With Breathtaking Mountain-lake Views!Get Rates
            Stylish Townhome With Hot Tub Conveniently Located to Area Attractions!

            Stylish Townhome With Hot Tub Conveniently Located to Area Attractions!

            , Oakland
               
               
              4.0 out of 5 (1 reviews)

              Situated in Oakland, this vacation home is 1.7 mi (2.8 km) from Deep Creek Lake State Park and within 9 mi (15 km) of Wisp Resort and Thousand Acres Lakeside ...

              Stylish Townhome With Hot Tub Conveniently Located to Area Attractions!Get Rates

              Stylish Townhome With Hot Tub Conveniently Located to Area Attractions!Get Rates
              The Tall Ceilings, Modern Upgrades, and Open Layout of Bear Foot Cove Make for Great Gatherings!

              The Tall Ceilings, Modern Upgrades, and Open Layout of Bear Foot Cove Make for Great Gatherings!

              , Oakland
                 
                 

                Situated in a rural location, this romantic vacation home is 6.1 mi (9.8 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Thousand ...

                The Tall Ceilings, Modern Upgrades, and Open Layout of Bear Foot Cove Make for Great Gatherings!Get Rates

                The Tall Ceilings, Modern Upgrades, and Open Layout of Bear Foot Cove Make for Great Gatherings!Get Rates
                Centrally Located Log Home With Indoor Hot Tub

                Centrally Located Log Home With Indoor Hot Tub

                , Oakland
                   
                   
                  5.0 out of 5 (2 reviews)

                  Situated in Oakland, this vacation home is 2.4 mi (3.8 km) from Deep Creek Lake State Park and within 9 mi (15 km) of Wisp Resort and Thousand Acres Lakeside ...

                  Centrally Located Log Home With Indoor Hot TubGet Rates

                  Centrally Located Log Home With Indoor Hot TubGet Rates
                  Quite Location Close to Area Activities

                  Quite Location Close to Area Activities

                  , Oakland
                     
                     

                    Situated in Oakland, this vacation home is 4 mi (6.4 km) from Wisp Resort and within 12 mi (20 km) of Deep Creek Lake State Park and Thousand Acres Lakeside ...

                    Quite Location Close to Area ActivitiesGet Rates

                    Quite Location Close to Area ActivitiesGet Rates
                    Easy Lake Access & Great Outdoor Space!

                    Easy Lake Access & Great Outdoor Space!

                    , Oakland
                       
                       

                      Situated in Oakland, this vacation home is within 12 mi (20 km) of Deep Creek Lake State Park, Wisp Resort, and Thousand Acres Lakeside Golf Course. Cranesville ...

                      Easy Lake Access & Great Outdoor Space!Get Rates

                      Easy Lake Access & Great Outdoor Space!Get Rates
                      At Creekside Lodge, the Mountain Aesthetic is Perfected With Rich Colors and Rugged Natural Textures

                      At Creekside Lodge, the Mountain Aesthetic is Perfected With Rich Colors and Rugged Natural Textures

                      , OAKLAND
                         
                         

                        Situated in a rural location, this romantic vacation home is 5 mi (8 km) from Wisp Resort and within 12 mi (20 km) of Deep Creek Lake State Park and Thousand ...

                        At Creekside Lodge, the Mountain Aesthetic is Perfected With Rich Colors and Rugged Natural TexturesGet Rates

                        At Creekside Lodge, the Mountain Aesthetic is Perfected With Rich Colors and Rugged Natural TexturesGet Rates
                        Discerning Guests Adore the Fetching Details and Upscale Furnishings at Overlook Mountain Villa 4B!

                        Discerning Guests Adore the Fetching Details and Upscale Furnishings at Overlook Mountain Villa 4B!

                        , MCHENRY
                           
                           
                          5.0 out of 5 (1 reviews)

                          Situated in a rural location, this romantic vacation home is 2 mi (3.2 km) from Wisp Resort and within 12 mi (20 km) of Deep Creek Lake State Park and Cranesville ...

                          Discerning Guests Adore the Fetching Details and Upscale Furnishings at Overlook Mountain Villa 4B!Get Rates

                          Discerning Guests Adore the Fetching Details and Upscale Furnishings at Overlook Mountain Villa 4B!Get Rates
                          Conveniently Located log Cabin With Outdoor hot Tub!

                          Conveniently Located log Cabin With Outdoor hot Tub!

                          , Oakland
                             
                             
                            4.3 out of 5 (3 reviews)

                            Situated in Oakland, this vacation home is 4.6 mi (7.4 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Thousand Acres Lakeside ...

                            Conveniently Located log Cabin With Outdoor hot Tub!Get Rates

                            Conveniently Located log Cabin With Outdoor hot Tub!Get Rates
                            Lakefront Home With 3 Master Suites & a Private Dock!

                            Lakefront Home With 3 Master Suites & a Private Dock!

                            , Oakland
                               
                               
                              4.7 out of 5 (3 reviews)

                              Situated on a lake, this vacation home is within 12 mi (20 km) of Deep Creek Lake State Park, Wisp Resort, and Cranesville Swamp Natural Area. Thousand Acres ...

                              Lakefront Home With 3 Master Suites & a Private Dock!Get Rates

                              Lakefront Home With 3 Master Suites & a Private Dock!Get Rates
                              Perfect for an Intimate Escape, Swallow Falls Inn Cabin 4 is Your Ideal Home Away From Home!

                              Perfect for an Intimate Escape, Swallow Falls Inn Cabin 4 is Your Ideal Home Away From Home!

                              , OAKLAND
                                 
                                 
                                4.0 out of 5 (1 reviews)

                                Situated in a rural location, this romantic vacation home is within 9 mi (15 km) of Cranesville Swamp Natural Area, Wisp Resort, and Deep Creek Lake State Park. ...

                                Perfect for an Intimate Escape, Swallow Falls Inn Cabin 4 is Your Ideal Home Away From Home!Get Rates

                                Perfect for an Intimate Escape, Swallow Falls Inn Cabin 4 is Your Ideal Home Away From Home!Get Rates
                                Adorable Chalet in Peaceful Setting With Multiple Game Tables!

                                Adorable Chalet in Peaceful Setting With Multiple Game Tables!

                                , Oakland
                                   
                                   
                                  4.5 out of 5 (4 reviews)

                                  Set in Oakland, this family-friendly vacation home is within 12 mi (20 km) of Deep Creek Lake State Park, Cranesville Swamp Natural Area, and Wisp Resort. Thousand ...

                                  Adorable Chalet in Peaceful Setting With Multiple Game Tables!Get Rates

                                  Adorable Chalet in Peaceful Setting With Multiple Game Tables!Get Rates
                                  Luxurious Townhome With Lake Views

                                  Luxurious Townhome With Lake Views

                                  , Oakland
                                     
                                     
                                    4.6 out of 5 (5 reviews)

                                    Situated in Oakland, this vacation home is 4.1 mi (6.7 km) from Wisp Resort and within 12 mi (20 km) of Deep Creek Lake State Park and Thousand Acres Lakeside ...

                                    Luxurious Townhome With Lake ViewsGet Rates

                                    Luxurious Townhome With Lake ViewsGet Rates
                                    Cheerful & Inviting 3 Bedroom Home w/ Hot Tub in the Heart of Deep Creek!

                                    Cheerful & Inviting 3 Bedroom Home w/ Hot Tub in the Heart of Deep Creek!

                                    , Oakland
                                       
                                       
                                      4.9 out of 5 (8 reviews)

                                      Situated in Oakland, this vacation home is 4.1 mi (6.6 km) from Wisp Resort and within 12 mi (20 km) of Deep Creek Lake State Park and Thousand Acres Lakeside ...

                                      Cheerful & Inviting 3 Bedroom Home w/ Hot Tub in the Heart of Deep Creek!Get Rates

                                      Cheerful & Inviting 3 Bedroom Home w/ Hot Tub in the Heart of Deep Creek!Get Rates
                                      Let the Good Times Roll in This New Orleans Inspired ski Chalet! This Home is Full of Flair!

                                      Let the Good Times Roll in This New Orleans Inspired ski Chalet! This Home is Full of Flair!

                                      , MCHENRY
                                         
                                         

                                        Situated in Oakland, this vacation home is 2.3 mi (3.8 km) from Wisp Resort and 9.2 mi (14.8 km) from Deep Creek Lake State Park. Cranesville Swamp Natural Area ...

                                        Let the Good Times Roll in This New Orleans Inspired ski Chalet! This Home is Full of Flair!Get Rates

                                        Let the Good Times Roll in This New Orleans Inspired ski Chalet! This Home is Full of Flair!Get Rates
                                        Mountain Majesty Comes to Life at Lost Bearadise. This Quaint Forest Cabin is as Charming as can be!

                                        Mountain Majesty Comes to Life at Lost Bearadise. This Quaint Forest Cabin is as Charming as can be!

                                        , Oakland
                                           
                                           

                                          Situated in a rural location, this romantic vacation home is within 12 mi (20 km) of Deep Creek Lake State Park, Cranesville Swamp Natural Area, and Cathedral ...

                                          Mountain Majesty Comes to Life at Lost Bearadise. This Quaint Forest Cabin is as Charming as can be!Get Rates

                                          Mountain Majesty Comes to Life at Lost Bearadise. This Quaint Forest Cabin is as Charming as can be!Get Rates
                                          Map

                                          Vacation Rentals in Oakland

                                          Search for Vacation Rentals in Oakland on Expedia.com! You can easily find your home rentals, villas, short-term apartments for rent in Oakland using one of the methods below: 

                                          • View our selection of featured home rentals in Oakland
                                          • Use the map to find apartments and other vacation rentals in the Oakland neighbourhood you prefer
                                          • Enter your travel dates to view the best deals on vacation rentals in Oakland while they last

                                          Look no further and take a look at our great range of rental properties in Oakland!

                                          Other types of properties in Oakland you may be interested in

                                          The Garrett Inn

                                          The Garrett Inn

                                          17848 Garrett Highway, Oakland
                                            2.5 out of 5.0
                                             
                                             

                                            Situated in Oakland, this motel is 4.7 mi (7.6 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Thousand Acres Lakeside Golf Course. ...

                                            The Garrett Inn$88

                                            The Garrett Inn$88
                                            Artic Retreat is one Tranquil Oasis! Embrace the Wild and Restless Energy of This Wooded Retreat!

                                            Artic Retreat is one Tranquil Oasis! Embrace the Wild and Restless Energy of This Wooded Retreat!

                                            , OAKLAND
                                               
                                               

                                              Situated in a rural location, this romantic vacation home is 2.3 mi (3.7 km) from Deep Creek Lake State Park and within 9 mi (15 km) of Wisp Resort and Thousand ...

                                              Inn At Deep Creek

                                              Inn At Deep Creek

                                              19638 Garrett Hwy, Oakland
                                                2.5 out of 5.0
                                                 
                                                 

                                                Located in the heart of Oakland, this hotel is 2.8 mi (4.5 km) from Deep Creek Lake State Park and within 9 mi (15 km) of Wisp Resort and Thousand Acres Lakeside ...

                                                Inn At Deep Creek$169

                                                Inn At Deep Creek$169
                                                Rustic and Warm, Bunbury Cottage is a Charming Lincoln-lodge Style Home With Lots to Offer!

                                                Rustic and Warm, Bunbury Cottage is a Charming Lincoln-lodge Style Home With Lots to Offer!

                                                , OAKLAND
                                                   
                                                   

                                                  Situated in a rural location, this romantic vacation home is 6 mi (9.6 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Cranesville ...