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

Vacation rentals in Oakland

Find 33 available house rentals from 12 partners
Anytime
Guests
Anytime
Guests

  • Price per night

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

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • 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 Recommended vacation rentals in Oakland

Find your perfect vacation rental in Oakland from just $99 per night!

House Oakland
-44%
Dec 13 - Dec 20
House ∙ 11 guests ∙ 3 bedrooms

House with terrace, jacuzzi & barbecue | Nature view

Oakland, West Oakland, Maryland, United States
$174$98
per night
$174$98
per night
View deal
House Oakland
Dec 14 - Dec 21
Free cancellation
House ∙ 6 guests ∙ 1 bedroom

House with barbecue & garden | Pet-friendly

Oakland, West Oakland, Maryland, United States
$115
per night
Excellent(8 ratings)
$115
per night
View deal
House Oakland
Jul 4 - Jul 11
House ∙ 12 guests ∙ 6 bedrooms

Wonderful house | Dogs allowed

Oakland, West Oakland, Maryland, United States
$450
per night
$450
per night
View deal
Motel Oakland
Jul 4 - Jul 11
Free cancellation
Motel ∙ 2 guests ∙ 1 bedroom

Motel

Oakland, West Oakland, Maryland, United States
$160
per night
$160
per night
View deal
Motel Oakland
Apr 26 - May 3
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 persons

Oakland, West Oakland, Maryland, United States
$103
per night
Outstanding
$103
per night
View deal
Motel Oakland
May 3 - May 10
Free cancellation
Motel ∙ 4 guests ∙ 1 bedroom

Motel | Perfect for remote work

Oakland, West Oakland, Maryland, United States
$116
per night
$116
per night
View deal
House Oakland
-51%
Jun 8 - Jun 15
Free cancellation
House ∙ 9 guests ∙ 3 bedrooms

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

Oakland, West Oakland, Maryland, United States
$362$178
per night
Outstanding(34 ratings)
$362$178
per night
View deal
Cabin Oakland
Jun 21 - Jun 28
Cabin ∙ 8 guests ∙ 3 bedrooms

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

Oakland, West Oakland, Maryland, United States
$163
per night
Outstanding(2 ratings)
$163
per night
View deal
House Oakland
-21%
Jun 6 - Jun 13
House ∙ 12 guests ∙ 4 bedrooms

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

Oakland, West Oakland, Maryland, United States
$400$317
per night
Excellent(23 ratings)
$400$317
per night
View deal
House Oakland
Jul 12 - Jul 19
House ∙ 10 guests ∙ 3 bedrooms

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

Oakland, West Oakland, Maryland, United States
$392
per night
Outstanding(6 ratings)
$392
per night
View deal
Lodge Oakland
Apr 26 - May 3
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
$175
per night
$175
per night
View deal
Lodge Oakland
Apr 26 - May 3
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with garden

Oakland, West Oakland, Maryland, United States
$175
per night
$175
per night
View deal
Lodge Oakland
Apr 26 - May 3
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
$175
per night
$175
per night
View deal
Lodge Oakland
Apr 26 - May 3
Lodge ∙ 2 guests ∙ 1 bedroom

Nice lodge with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
$185
per night
$185
per night
View deal
Farmhouse Oakland
Jun 14 - Jun 21
Farmhouse ∙ 12 guests ∙ 6 bedrooms

Fully equipped farm with sauna, patio & hot tub

Oakland, West Oakland, Maryland, United States
$597
per night
Excellent(8 ratings)
$597
per night
View deal

Vacation houses with Balconies or Patios

House Oakland
from $200
per night
House ∙ 11 guests ∙ 4 bedrooms

Nice vacation home with hot tub, patio & barbeque | Lake view | Pets allowed

4.3
Very good(8 ratings)
Oakland, West Oakland, Maryland, United States
Balcony/Patio
View deal
House Oakland
from $249
per night
House ∙ 6 guests ∙ 2 bedrooms

House with barbeque & terrace

3.7
Good(6 ratings)
Oakland, West Oakland, Maryland, United States
Balcony/Patio
View deal
House Oakland
from $156
per night
House ∙ 2 guests ∙ 1 bedroom

House with garden & grill

5.0
Outstanding(4 ratings)
Oakland, West Oakland, Maryland, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with Wi-Fi

House Oakland
from $199
per night
House ∙ 2 guests ∙ 1 bedroom

House with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
Internet
View deal
House Oakland
from $257
per night
House ∙ 4 guests ∙ 2 bedrooms

Pleasant vacation home with 2 rooms for 4 persons

Oakland, West Oakland, Maryland, United States
Internet
View deal
House Oakland
from $283
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with 3 rooms for 6 persons

Oakland, West Oakland, Maryland, United States
Internet
View deal
See all offers

Apartments and vacation rentals with a kitchen

House Oakland
from $113
per night
House ∙ 9 guests ∙ 4 bedrooms

House | Pet-friendly

Oakland, West Oakland, Maryland, United States
Kitchen
View deal
House Oakland
from $682
per night
House ∙ 10 guests ∙ 3 bedrooms

House with 3 rooms for 10 persons

Oakland, West Oakland, Maryland, United States
Kitchen
View deal
House Oakland
from $118
per night
House ∙ 9 guests ∙ 4 bedrooms

House with 4 rooms for 9 persons

Oakland, West Oakland, Maryland, United States
Kitchen
View deal
See all offers

Budget-friendly Vacation Rentals in Oakland

Find Fantastic yet Inexpensive Offers

Motel Oakland
Jul 4 - Jul 11
$144
per night
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 persons

4.5
Excellent(51 ratings)
Oakland, West Oakland, Maryland, United States
View deal
House Oakland
from $290
per night
House ∙ 11 guests ∙ 3 bedrooms

Child-friendly house

Oakland, West Oakland, Maryland, United States
View deal

Customer ratings and reviews

How are reviews collected?
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 $754
per night
HomeToGo
House ∙ 18 guests ∙ 7 bedrooms
4.0
Very good(1 rating)
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 $340
per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
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 $747
per night
HomeToGo
House ∙ 10 guests ∙ 5 bedrooms
4.9
Outstanding(7 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 $600
per night
HomeToGo
House ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent(12 ratings)
Oakland, West Oakland, Maryland, United States
View deal
Show more

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Popular Rental Amenities in Oakland

  • Pet-friendly (8)
  • WiFi (33)
  • Fireplace (18)
  • Air conditioning (25)
  • Hot tub (10)
  • TV (24)
  • Kitchen (23)
  • Grill (10)
  • No pets (25)
  • Fishing (7)
  • Balcony/patio (8)
  • Dishwasher (11)

Oakland is a perfect vacation spot for pet owners, as 8 properties in Oakland allow you to bring your pet. In addition, pet-friendly accommodations in Oakland cost, on average, $456 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 $560 (12/27 – 1/3) in Oakland. Vacation rental prices go down to $477 per night in April (4/26 – 5/3).

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 April (4/4 – 4/11), as 79% of the rentals are booked. May (5/10 – 5/17) 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.

What are the best places to discover the arts and culture of Oakland?

Historical Oakland

Although there are various sites to explore in Oakland, there are some things that should not be missed. Listed on National Register of Historic Places, B&O Railroad Museum is one of the oldest structures of Oakland and it is both an educational and atmospheric attraction.

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

🏡 Vacation rentals available 33 rentals
🌙 Nightly prices starting at $99
⭐ Popular amenities Pets allowed, Internet and Fireplace
🐾 Pet friendly homes 8 homes
15,111 reviews
Oakland vacation rentals have an average rating of 4.4/5 on 15,111 reviews left by travelers.

Frequently Asked Questions

What is the average nightly price for a vacation home in Oakland?

The average accommodation in Oakland is priced at $99 per night. Average prices for house rentals are $512 per night. Cabins in Oakland cost $942 per night on average.

How many vacation homes are available to book in Oakland?

There are 33 rentals in Oakland to choose from and book for your next trip.

What are the most popular amenities for vacation homes in Oakland?

If you're looking to book a vacation rental in Oakland, others search for homes with these amenities: Internet, Pets allowed and Fireplace.

Are dogs allowed in vacation rentals in Oakland?

Yes, there are 8 vacation rentals in Oakland that allow dogs , with an average nightly price of $456.

What's the best time of year to travel to Oakland?

July and August are the warmest months in Oakland with temperatures around 75 °F. The coldest months in Oakland are January and February, with 19 °F on average.

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