Vacation rentals in Oakland - HomeToGo base64Hash Vacation rentals in Oakland - HomeToGo

Vacation rentals in Oakland

Browse 21 available vacation homes and compared across 13 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Services

    • Pool
    • WiFi
    • Fireplace
    • Air conditioning
    • Hot tub
    • TV
    • Kitchen
    • Balcony/patio
    • Dishwasher
    • Washing machine
    • Yard
    • Microwave
    • Parking
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No pets
    • No smoking
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Oakland

Discover your ideal Oakland vacation rental with real-time comparisons of 21 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Oakland
House ∙ 9 guests ∙ 4 bedrooms

House | Pet-friendly

Oakland, West Oakland, Maryland, United States
This Oakland house rental accommodates 9 guests, welcomes pets, and offers a perfect base for exploring the vibrant city.
from $110
per night
from $110
per night
View deal
Mobile home Oakland
Mobile home ∙ 2 guests ∙ 1 bedroom

Mobile home with barbeque

Oakland, West Oakland, Maryland, United States
This RV rental in Oakland features a kitchen and parking, perfect for a cozy getaway for two in a vibrant city.
from $188
per night
Outstanding(6 ratings)
from $188
per night
View deal
Cabin Oakland
Cabin ∙ 4 guests ∙ 1 bedroom

Cabin with patio & barbeque

Oakland, West Oakland, Maryland, United States
This Oakland cabin invites up to four guests and their pets to unwind in nature, creating unforgettable vacation memories.
from $139
per night
from $139
per night
View deal
House Oakland
House ∙ 6 guests ∙ 2 bedrooms

House with barbeque & terrace

Oakland, West Oakland, Maryland, United States
This family-friendly house rental in Oakland offers a kitchen for home-cooked meals and ample space for six guests to relax.
from $222
per night
Good(6 ratings)
from $222
per night
View deal
Cabin Oakland
Cabin ∙ 13 guests ∙ 4 bedrooms

Cabin with patio, yard & BBQ

Oakland, West Oakland, Maryland, United States
This Oakland cabin features a hot tub, fireplace, and spacious yard, perfect for families and groups of up to 13 guests.
from $334
per night
Good(7 ratings)
from $334
per night
View deal
Lodge Oakland
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
This Oakland lodge features a fireplace and spa, providing a cozy retreat for two with convenient parking.
from $223
per night
from $223
per night
View deal
House Oakland
House ∙ 15 guests ∙ 5 bedrooms

Family-friendly wonderful house with grill, patio & hot tub | Mountain view

Oakland, West Oakland, Maryland, United States
This waterfront house rental in Oakland features a kitchen, hot tub, balcony, and mountain views, perfect for up to 15 guests.
from $763
per night
from $763
per night
View deal
Farmhouse Oakland
Farmhouse ∙ 12 guests ∙ 6 bedrooms

Fully equipped farm with sauna, patio & hot tub

Oakland, West Oakland, Maryland, United States
This farmhouse rental in Oakland features a sauna, hot tub, fireplace, and a yard, perfect for gatherings of up to 12 guests.
from $452
per night
Excellent(8 ratings)
from $452
per night
View deal
Mobile home Oakland
Mobile home ∙ 2 guests ∙ 1 bedroom

Mobile home with BBQ

Oakland, West Oakland, Maryland, United States
This RV rental in Crellin offers a kitchen, balcony, and parking for a perfect getaway with your travel companion.
from $152
per night
Outstanding(2 ratings)
from $152
per night
View deal
Chalet Oakland
Chalet ∙ 13 guests ∙ 5 bedrooms

Family-oriented chalet with jacuzzi, grill & patio | Lake view | Dogs allowed

Oakland, West Oakland, Maryland, United States
This waterfront chalet in Oakland features a hot tub, fireplace, kitchen, and space for 13, perfect for family gatherings.
from $326
per night
Very good(16 ratings)
from $326
per night
View deal
Farmhouse Oakland
Farmhouse ∙ 2 guests ∙ 1 bedroom

Farm with garden & grill

Oakland, West Oakland, Maryland, United States
This Crellin farmhouse rental features a kitchen, balcony, and parking, perfect for a cozy getaway for two.
from $189
per night
Outstanding(14 ratings)
from $189
per night
View deal
House Oakland
House ∙ 12 guests ∙ 4 bedrooms

Family-oriented house with terrace, BBQ & jacuzzi | Mountain view | Pets allowed

Oakland, West Oakland, Maryland, United States
This family-friendly waterfront house in Oakland features a kitchen, fireplace, hot tub, and mountain views, perfect for 12 guests.
from $300
per night
Excellent(25 ratings)
from $300
per night
View deal
Lodge Oakland
Lodge ∙ 2 guests ∙ 1 bedroom

Charming lodge with garden

Oakland, West Oakland, Maryland, United States
This cozy lodge in Oakland features a fireplace, spa, yard, and parking, perfect for a romantic getaway for two.
from $210
per night
from $210
per night
View deal
Cabin Oakland
Cabin ∙ 6 guests ∙ 3 bedrooms

Cabin with jacuzzi & patio

Oakland, West Oakland, Maryland, United States
This cabin in Mountain Lake Park features a hot tub, fireplace, and kitchen, welcoming up to six guests and their pets.
from $230
per night
Outstanding(5 ratings)
from $230
per night
View deal
Lodge Oakland
Lodge ∙ 8 guests ∙ 3 bedrooms

Children-friendly charming lodge with barbeque, terrace & heated pool | Dogs allowed

Oakland, West Oakland, Maryland, United States
This lodge in Terra Alta features a heated pool, fireplace, and kitchen, accommodating up to 8 guests, including pets.
from $257
per night
Outstanding(24 ratings)
from $257
per night
View deal

Vacation rentals with a balcony

Lodge Oakland
from $236
per night
Lodge ∙ 2 guests ∙ 1 bedroom

Nice lodge with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
Balcony
View deal
House Oakland
from $298
per night
House ∙ 12 guests ∙ 4 bedrooms

Vacation home with jacuzzi, barbeque & pool | Lake view

5.0
Outstanding(2 ratings)
Oakland, West Oakland, Maryland, United States
Balcony
View deal
Resort Oakland
from $167
per night
Resort ∙ 2 guests ∙ 1 bedroom

Holiday park with terrace & grill

5.0
Outstanding(17 ratings)
Oakland, West Oakland, Maryland, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

House Oakland
from $288
per night
House ∙ 9 guests ∙ 3 bedrooms

Child-friendly spacious house with patio, garden & barbeque | Pet-friendly

5.0
Outstanding(79 ratings)
Oakland, West Oakland, Maryland, United States
Fireplace
View deal
Lodge Oakland
from $232
per night
Lodge ∙ 2 guests ∙ 1 bedroom

Vacation home | Lake view

Oakland, West Oakland, Maryland, United States
Fireplace
View deal
Apartment Oakland
from $204
per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment with pool, terrace & barbeque | Nature view | Good for workation

5.0
Outstanding(10 ratings)
Oakland, West Oakland, Maryland, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Oakland offering exceptional value for money

Lodge Oakland
from $223
per night
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with garden

Oakland, West Oakland, Maryland, United States
View deal
Cabin Oakland
from $340
per night
Cabin ∙ 12 guests ∙ 4 bedrooms

Cottage with 4 rooms for 12 persons

Oakland, West Oakland, Maryland, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Oakland

How are reviews collected?
Marlon S.
Guest verified by HomeToGo

This cabin was a fantastic find! Spotlessly clean, with modern amenities that made our stay comfortable and enjoyable. The sleek design and well-maintained space added a touch of luxury to our getaway. Highly recommend!

Reviewed on 10/14/2025 | Group
Cabin Oakland
from $502
per night
Cabin ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(3 ratings)
Oakland, West Oakland, Maryland, United States
View deal
Diane B.
Guest verified by HomeToGo

This house is beautiful and had great access to the lake. The only issue we had was with the bedroom situation on the lower level. It was obvious that the parents wanted to sleep on the same level as their kids (with the bunk beds) but the bedroom across from the room with the bunk beds only provided a DOUBLE bed mattress which was HORRIBLE! It was like sleeping on a huge marshmallow! The room was extremely small (unlike the pictures) and the tv was situated next to the door which was a head injury waiting to happen. If you don't have to use the two lower level bedrooms, then the house is amazing!

Reviewed on 8/22/2025 | Family
House Oakland
from $927
per night
House ∙ 14 guests ∙ 5 bedrooms
4.9
Outstanding(31 ratings)
Oakland, West Oakland, Maryland, United States
View deal
Dan V.
Guest verified by HomeToGo

The cabin was absolutely beautiful! It was just liked the pictures. Very clean and excellent location. The only tiny little comment I have is housekeeping needs to clean the ceiling fans and the air vents. They were pretty disgusting BUT everything else was beautiful and perfect!

Reviewed on 6/29/2025 | Group
House Oakland
from $606
per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(140 ratings)
Oakland, West Oakland, Maryland, United States
View deal
Matthew B.
Guest verified by HomeToGo

House was awesome ! Looks like they were in the middle of upgrading stuff ! But will definitely be making a trip back in the summer to enjoy the lake !

Reviewed on 4/15/2025 | Family
House Oakland
from $814
per night
House ∙ 18 guests ∙ 7 bedrooms
4.6
Excellent(19 ratings)
Oakland, West Oakland, Maryland, United States
View deal
kris l.
Guest verified by HomeToGo

This home was absolutely gorgeous. Couldn’t be in a better location to enjoy the views close to restaurants, water activities, state parks, plus so much more.

Reviewed on 10/5/2024 | Family
House Oakland
from $335
per night
House ∙ 10 guests ∙ 3 bedrooms
4.4
Very good(28 ratings)
Oakland, West Oakland, Maryland, United States
View deal
Holly M.
Guest verified by HomeToGo

The house was very nice, 4 large bedrooms with ensuite baths and the 5th br was a small trundle room (no bathroom access except in another bedroom). The kitchen had everything we needed except a muffin pan. Would love an instant pot, but I brought my own. It is a short walk to the dock. Hot tub was great as was the screened porch. We had 2 items that needed attention and they were addressed within an hour or two. We would love to vacation there again!

Reviewed on 7/23/2024 | Family
House Oakland
from $780
per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(14 ratings)
Oakland, West Oakland, Maryland, United States
View deal
Tanya M.
Guest verified by HomeToGo

This is the ultimate weekend getaway! My family and I had a wonderfully relaxing weekend. The house easily accomodates a family of 6 adults with plenty of space for more. The location is unbeatable and with access to the lake, we had no need to leave the property. The "stock the fridge" offer by the management company enabled us to get settled quickly and enjoyed cooking in the spacious kitchen with a view of the lake. Highly recommend!

Reviewed on 7/15/2023 | Family
House Oakland
from $1,192
per night
House ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent(21 ratings)
Oakland, West Oakland, Maryland, United States
View deal
Show more

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Popular Features & Amenities in Oakland

  • Pet-friendly (5)
  • Pool (1)
  • WiFi (17)
  • Fireplace (7)
  • Air conditioning (17)
  • Hot tub (4)
  • TV (15)
  • Kitchen (7)
  • Grill (5)
  • No pets (14)
  • Fishing (5)
  • Balcony/patio (4)

Oakland is a perfect vacation spot for pet owners, as 5 properties in Oakland allow you to bring your pet. In addition, pet-friendly accommodations in Oakland cost, on average, $342 per night. You will also find different accommodation options if you would like to stay near the city center, as a few of the pet-friendly accommodations are less than 2 mile away from the center of the city (0).

Price and Availability Index in Oakland

Click on any bar to see price and availability information

Vacation Rental Price Information in Oakland

The price graph will give you the average nightly price for the upcoming months of the year in Oakland. The average nightly rate for vacation homes can go up to $751 (8/8 – 8/15) in Oakland. Vacation rental prices go down to $575 per night in April (4/11 – 4/18).

Rental availability information in Oakland

The graph above shows the typical availability of vacation rentals in Oakland. It is harder to find an accommodation during a week of January (1/30 – 2/6), as 91% of the rentals are booked. March (3/14 – 3/21) has got the highest percentage of available rentals.

Your vacation home in Oakland awaits you!

If you enjoy falling asleep under the stars between the trees along with a campfire, and yet don't want to give up your comfort of home, you will be pleased with the mountain cabins in Oakland. After a joyful trekking at the Garret State Forest, tree cabins will relieve your tiredness and make you feel at home.

Where are the unique attractions in Oakland?

Activities in Oakland

State parks such as Swallow Falls, located at the Youghiogheny River 9 miles north Oakland, and Deep Creek Lake, located 18 miles south of Route 219, are just two of many attractions where you can discover the nature of the region. Downhill skiing, kayaking, atv renting, and fishing are just some of the unique experiences that you can make in Oakland.

Information about vacation rentals in Oakland

🌙 Nightly prices starting at $110
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 5 homes
🏊 Vacation rentals with pools 2 homes
39 reviews
Oakland vacation rentals have an average rating of 4.5/5 on 39 reviews left by travelers.

Frequently Asked Questions

What is the nightly price for a vacation rental in Oakland?

The price of a night's stay in Oakland starts at $110. $939 is the average nightly price for house rentals in Oakland. Condos in Oakland cost $268 per night on average.

How many vacation rentals are available for booking in Oakland?

There are 21 vacation rentals from 13 different providers in Oakland.

What amenities are most popular for vacation homes in Oakland?

Three most popular amenities for home rentals in Oakland include accommodations with: Pets allowed, Pool, and Internet.

Are pets allowed in vacation homes in Oakland?

In case if you are traveling with a dog in Oakland - 24% of rentals allow pets.

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