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

Vacation rentals in Oakland

Browse 19 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+

  • Booking Options

    • Instant Booking

  • 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 19 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Oakland
House ∙ 11 guests ∙ 3 bedrooms

House with terrace, jacuzzi & barbecue | Nature view

Oakland, West Oakland, Maryland, United States
This waterfront house in Oakland features a hot tub, fireplace, and mountain views, perfect for family gatherings and pets.
from $186
per night
Excellent(19 ratings)
from $186
per night
View deal
House Oakland
House ∙ 14 guests ∙ 4 bedrooms

Vacation home with yard, jacuzzi & terrace | Lake view

Oakland, West Oakland, Maryland, United States
This waterfront house in Oakland features a hot tub, fireplace, and mountain views, perfect for families and pets alike.
from $285
per night
Outstanding(31 ratings)
from $285
per night
View deal
House Oakland
House ∙ 12 guests ∙ 6 bedrooms

Wonderful house | Dogs allowed

Oakland, West Oakland, Maryland, United States
This Oakland house rental accommodates 12, featuring a fireplace, pet-friendly policies, and ample parking for a perfect getaway.
from $172
per night
Outstanding(3 ratings)
from $172
per night
View deal
House Oakland
House ∙ 34 guests ∙ 10 bedrooms

House with jacuzzi, barbeque & private pool | Mountain view

Oakland, West Oakland, Maryland, United States
This Oakland house rental offers a private pool, hot tub, and mountain views, perfect for a family getaway with 34 guests.
from $1,695
per night
Good(20 ratings)
from $1,695
per night
View deal
House Oakland
House ∙ 4 guests ∙ 1 bedroom

Lovely vacation home with grill & garden | Pet-friendly

Oakland, West Oakland, Maryland, United States
This Oakland house rental features a cozy fireplace, a yard for pets, and convenient parking, perfect for a memorable getaway.
from $110
per night
Excellent(2 ratings)
from $110
per night
View deal
House Oakland
House ∙ 12 guests ∙ 4 bedrooms

House with barbeque, jacuzzi & patio | Lake view | Good for workation

Oakland, West Oakland, Maryland, United States
This waterfront house in Oakland features a pool, hot tub, and balcony, perfect for family gatherings of up to 12.
from $299
per night
Outstanding(2 ratings)
from $299
per night
View deal
House Oakland
House ∙ 9 guests ∙ 3 bedrooms

Vacation home with grill & hot tub | Perfect for remote work

Oakland, West Oakland, Maryland, United States
This house rental in Oakland features a hot tub, fireplace, and a kitchen, perfect for family gatherings and events.
from $257
per night
from $257
per night
View deal
House Oakland
House ∙ 4 guests ∙ 1 bedroom

Vacation home with barbeque | Pet-friendly

Oakland, West Oakland, Maryland, United States
This Oakland house rental features a fireplace, parking, and is pet-friendly, perfect for a getaway with family or friends.
from $110
per night
Outstanding(1 rating)
from $110
per night
View deal
House Oakland
House ∙ 9 guests ∙ 3 bedrooms

Child-friendly spacious vacation home with jacuzzi, garden & patio | Pets are welcome

Oakland, West Oakland, Maryland, United States
This family-friendly house rental in Oakland features a hot tub, yard, and fireplace, accommodating up to nine guests and pets.
from $258
per night
Outstanding(79 ratings)
from $258
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 $253
per night
Outstanding(23 ratings)
from $253
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 $238
per night
Outstanding(4 ratings)
from $238
per night
View deal
Chalet Oakland
Chalet ∙ 13 guests ∙ 5 bedrooms

Family-oriented chalet with 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 $497
per night
Very good(8 ratings)
from $497
per night
View deal
House Oakland
House ∙ 10 guests ∙ 3 bedrooms

Family-oriented charming house with hot tub, barbecue & patio | Lake view | Dogs allowed

Oakland, West Oakland, Maryland, United States
This waterfront house rental in Oakland features a hot tub, balcony, and mountain views, perfect for family gatherings of 10.
from $301
per night
Outstanding(10 ratings)
from $301
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 $299
per night
Excellent(24 ratings)
from $299
per night
View deal
House Oakland
House ∙ 4 guests ∙ 1 bedroom

Vacation home with garden & barbecue | Pets allowed

Oakland, West Oakland, Maryland, United States
This Oakland house rental features a fireplace, kitchen, yard, and pet-friendly options, accommodating up to four guests.
from $110
per night
Outstanding(1 rating)
from $110
per night
View deal

Vacation Rentals With Fireplaces

House Oakland
from $110
per night
House ∙ 4 guests ∙ 1 bedroom

Vacation home with yard & BBQ | Pets allowed

3.8
Good(2 ratings)
Oakland, West Oakland, Maryland, United States
Fireplace
View deal
Lodge Oakland
from $223
per night
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with garden

Oakland, West Oakland, Maryland, United States
Fireplace
View deal
Lodge Oakland
from $223
per night
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 room for 2 persons

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

Cabin Oakland
from $341
per night
Cabin ∙ 12 guests ∙ 4 bedrooms

Cottage with 4 rooms for 12 persons

Oakland, West Oakland, Maryland, United States
View deal
Lodge Oakland
from $235
per night
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 room for 2 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 $460
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 $860
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 $798
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 $311
per night
House ∙ 10 guests ∙ 3 bedrooms
4.4
Very good(26 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 $732
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 $1,151
per night
House ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent(21 ratings)
Oakland, West Oakland, Maryland, United States
View deal
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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, $336 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 $746 (8/1 – 8/8) in Oakland. Vacation rental prices go down to $498 per night in May (5/2 – 5/9).

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 December (12/12 – 12/19), as 92% of the rentals are booked. May (5/2 – 5/9) 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.

37 reviews
Oakland vacation rentals have an average rating of 4.4/5 on 37 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 $109. $933 is the average nightly price for house rentals in Oakland. Cabins in Oakland cost $942 per night on average.

How many vacation rentals are available for booking in Oakland?

There are 19 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 - 26% of rentals allow pets.

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