Estia Villas - Vacation Rentals in Oakland
Villa
9.6
(
5 Reviews
)
4 Bedrooms
4 Bathrooms
9 Guests
-
Hot Tub -
Parking -
Balcony/Terrace -
Kitchen
US $312
/Night
7 Nights - $2,184
House
5 Bedrooms
6 Bathrooms
12 Guests
2734.03 ft²
-
Parking
-
Skiing -
Air Conditioner -
Internet
US $669
/Night
7 Nights - $4,686
Villa
9.6
(
5 Reviews
)
3 Bedrooms
3 Bathrooms
9 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $326
/Night
7 Nights - $2,280
Villa
4 Bedrooms
3 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Spa -
Balcony/Terrace
US $506
/Night
7 Nights - $3,544
See More Oakland Vacation Rentals
Luxury Places to Stay in Oakland
Over 1198+
Luxury Places to Stay in or Near Oakland
House
9 Bedrooms
10 Bathrooms
25 Guests
6318.42 ft²
-
Private Pool -
Parking
-
Pool -
Skiing
US $2,522
/Night
7 Nights - $17,652
House
8.8
(
8 Reviews
)
9 Bedrooms
9 Bathrooms
25 Guests
6313 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $2,276
/Night
7 Nights - $15,935
House
8.6
(
8 Reviews
)
9 Bedrooms
8 Bathrooms
24 Guests
5362 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $1,918
/Night
7 Nights - $13,425
House
6.0
(
1 Review
)
6 Bedrooms
4 Bathrooms
16 Guests
4773 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,815
/Night
7 Nights - $12,702
House
6.8
(
5 Reviews
)
8 Bedrooms
7 Bathrooms
19 Guests
5744 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,691
/Night
7 Nights - $11,838
House
9 Bedrooms
9 Bathrooms
24 Guests
5360.43 ft²
-
Private Pool
-
Parking
-
Pool
-
Skiing
US $1,656
/Night
7 Nights - $11,593
House
9.0
(
49 Reviews
)
8 Bedrooms
8 Bathrooms
24 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,646
/Night
7 Nights - $11,523
See More Oakland Luxury Vacation Rentals
Find More Oakland Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Oakland
Over 304+
Top-Rated Vacation Rentals with a Pool in or Near Oakland
House
10.0
(
138 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
4000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $552
/Night
7 Nights - $3,864
House
10.0
(
63 Reviews
)
5 Bedrooms
4 Bathrooms
14 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $768
/Night
7 Nights - $5,375
Cottage
10.0
(
41 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
480 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $346
/Night
7 Nights - $2,419
House
10.0
(
22 Reviews
)
3 Bedrooms
3 Bathrooms
7 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $499
/Night
7 Nights - $3,493
Cabin
10.0
(
19 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $368
/Night
7 Nights - $2,578
House
10.0
(
16 Reviews
)
3 Bedrooms
3 Bathrooms
7 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $499
/Night
7 Nights - $3,493
Cabin
10.0
(
14 Reviews
)
4 Bedrooms
3 Bathrooms
15 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $838
/Night
7 Nights - $5,869
House
10.0
(
13 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $712
/Night
7 Nights - $4,983
See More Oakland Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Oakland
Over 328+
Pet-Friendly Vacation Rentals in or Near Oakland
House
9.6
(
30 Reviews
)
5 Bedrooms
3 Bathrooms
16 Guests
1852 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
US $716
/Night
7 Nights - $5,011
Cabin
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $260
/Night
7 Nights - $1,820
House
7.0
(
37 Reviews
)
5 Bedrooms
3 Bathrooms
14 Guests
2052 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $573
/Night
7 Nights - $4,010
House
9.8
(
79 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
2466 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $584
/Night
7 Nights - $4,086
Cabin
9.8
(
61 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
1400 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $392
/Night
7 Nights - $2,746
House
9.4
(
48 Reviews
)
5 Bedrooms
4 Bathrooms
14 Guests
2980 ft²
-
Hot Tub
-
Parking
-
Spa
-
Balcony/Terrace
US $688
/Night
7 Nights - $4,816
House
9.0
(
56 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
1765 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $540
/Night
7 Nights - $3,781
See More Pet-Friendly Vacation Rentals in Oakland on PetFriendly.io
Large Vacation Homes & Villas in Oakland
Over 624+
Large Vacation Homes & Villas in or Near Oakland
House
9.6
(
60 Reviews
)
4 Bedrooms
4 Bathrooms
11 Guests
1977 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
View
US $457
/Night
7 Nights - $3,200
US $605
/Night
7 Nights - $4,237
Ski Chalet
10.0
(
121 Reviews
)
5 Bedrooms
3 Bathrooms
15 Guests
2701 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $593
/Night
7 Nights - $4,152
House
9.2
(
23 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
1800 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $490
/Night
7 Nights - $3,428
House
9.2
(
32 Reviews
)
5 Bedrooms
4 Bathrooms
14 Guests
3846 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $864
/Night
7 Nights - $6,048
House
8.4
(
16 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
2592 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $535
/Night
7 Nights - $3,746
House
9.6
(
14 Reviews
)
8 Bedrooms
5 Bathrooms
22 Guests
3886 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
US $907
/Night
7 Nights - $6,348
House
9.4
(
21 Reviews
)
9 Bedrooms
7 Bathrooms
28 Guests
5178 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,468
/Night
7 Nights - $10,274
See More Family Vacation Rentals in Oakland on FVR
Wheelchair Accessible Vacation Homes in Oakland
Over 95+
Wheelchair Accessible Vacation Homes in or Near Oakland
Condo
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
382 ft²
-
Parking
-
Spa
-
Kitchen
-
Air Conditioner
US $258
/Night
7 Nights - $1,804
House
4 Bedrooms
4 Bathrooms
10 Guests
-
Hot Tub
-
Breakfast -
Parking
-
Skiing
US $694
/Night
7 Nights - $4,856
Condo
9.0
(
9 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $130
/Night
7 Nights - $910
Condo
10.0
(
3 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $421
/Night
7 Nights - $2,947
Condo
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $295
/Night
7 Nights - $2,062
Condo
10.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $493
/Night
7 Nights - $3,453
Condo
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $353
/Night
7 Nights - $2,468
Condo
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $307
/Night
7 Nights - $2,146
Oakland Vacation Rentals and Airbnb Places to Stay Under $200
Over 80+
Oakland Vacation Rentals and Airbnb Places to Stay Under $200
Cabin
10.0
(
3 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $173
/Night
7 Nights - $1,209
Apartment
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
376.74 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Child Friendly
US $186
/Night
7 Nights - $1,304
House
1 Bedroom
1 Bathroom
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $179
/Night
7 Nights - $1,253
House
4.4
(
27 Reviews
)
3 Bedrooms
3 Bathrooms
12 Guests
1296 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $138
/Night
7 Nights - $966
Condo
8.2
(
84 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
950 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $160
/Night
7 Nights - $1,118
House
4.5
(
27 Reviews
)
3 Bedrooms
5 Bathrooms
10 Guests
2115 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $138
/Night
7 Nights - $966
Condo
4.4
(
38 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
850 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $136
/Night
7 Nights - $952
House
4.4
(
8 Reviews
)
3 Bedrooms
4 Bathrooms
10 Guests
1840 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $139
/Night
7 Nights - $973
See More Oakland Vacation Rental Deals
Instantly Bookable Vacation Homes in Oakland
Over 647+
Instantly Bookable Vacation Homes in or Near Oakland
Cabin
9.4
(
19 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
860 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $398
/Night
7 Nights - $2,786
House
10.0
(
1 Review
)
3 Bedrooms
1 Bathroom
6 Guests
-
Spa
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $160
/Night
7 Nights - $1,120
Cabin
9.6
(
68 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
1788 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
US $674
/Night
7 Nights - $4,720
House
9.6
(
31 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1920 ft²
-
Hot Tub
-
Pool
-
Balcony/Terrace
-
Kitchen
US $373
/Night
7 Nights - $2,612
House
9.6
(
49 Reviews
)
5 Bedrooms
5 Bathrooms
14 Guests
3873 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $692
/Night
7 Nights - $4,844
House
8.4
(
7 Reviews
)
8 Bedrooms
6 Bathrooms
24 Guests
4909 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,358
/Night
7 Nights - $9,504
Cabin
9.4
(
203 Reviews
)
2 Bedrooms
1 Bathroom
8 Guests
984 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $407
/Night
7 Nights - $2,846
House
9.4
(
14 Reviews
)
7 Bedrooms
6 Bathrooms
22 Guests
4442 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
US $1,039
/Night
7 Nights - $7,275
See More Oakland Short-Term Vacation Rentals
About Oakland Vacation Rentals
With more than 4 Oakland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Oakland.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Oakland, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Oakland. Places to stay near Oakland are 683.51 ft² on average, with prices averaging US $453 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Oakland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Use these Quick Filters to Find a Vacation Rental in Oakland
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Oakland.
Weather in Oakland
View the weather forecast for Oakland before booking your Oakland Vacation Rentals to confirm your best time to go.
December - February
High 50°F Low 20°F
March - May
High 69°F Low 25°F
June - August
High 81°F Low 56°F
September - November
High 73°F Low 30°F
Top Attractions Around Oakland, MD
Estiavillas offers a large selection of top attractions around Oakland. Research things to do on your vacation before you visit Oakland.
Deep Creek Lake
Swallow Falls State Park
Garrett Regional Medical Center
Deep Creek Lake State Park
Ohiopyle State Park
Blackwater Falls State Park
Wisp Resort
Canaan Valley Ski Resort
Dolly Sods Wilderness Area
Lady Luck Casino at Nemacolin
Coopers Rock State Forest
Timberline Four Season Resort
Blackwater Falls
Hovatter's Wildlife Zoo
Youghiogheny River Lake
New Germany State Park
Janet and Imre Szilagyi Center for the Visual and Performing Arts
Off-Road Driving Academy
Funland
Other Places to Stay Near Oakland, MD
Silver Ridge
1,984 Properties
The View
1,822 Properties
Altamont
1,076 Properties
Thayerville
648 Properties
Mountain Lake Park
209 Properties
Garrett Regional Medical Center
153 Properties
Timbers on the Yough
139 Properties
Swallow Falls State Park
85 Properties
Mountainside
72 Properties
Blakeslee
49 Properties
Deep Creek Lake
45 Properties
Paradise Point
33 Properties
Complexes around Oakland, MD
Loft Oakland
37 Properties
Lakefront Fireplace
6 Properties
Lakefront Dock
4 Properties
Bear Lodge
2 Properties
Lakefront Efficiency
2 Properties
The Stars
2 Properties
Grove
1 Properties
Heart Soul
1 Properties
La Bella Vita
1 Properties
Memory Lane
1 Properties
Penn Cove Dreams
1 Properties
Runnin Dream
1 Properties
Serenity Summit
1 Properties
Sunrise
1 Properties
Oakland Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Oakland?
There are a lot of options in Oakland. If you plan on staying in the Oakland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oakland:
How many vacation rentals have private pools in Oakland?
There are 58 vacation rentals with private pools near Oakland. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Oakland are best for families?
If you are looking for a family-friendly vacation home in Oakland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oakland:
How many vacation rentals are available in Oakland?
Currently, the total number of properties listed in 2026 is over 4 in the Oakland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Oakland.
