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

Vacation rentals in Oakland

Find 28 available vacation homes 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 $113 per night!

Cabin Oakland
Cabin ∙ 6 guests ∙ 3 bedrooms

Cabin with jacuzzi & patio

Oakland, West Oakland, Maryland, United States
from $255
per night
Outstanding(1 rating)
from $255
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
from $371
per night
Outstanding(7 ratings)
from $371
per night
View deal
House Oakland
House ∙ 12 guests ∙ 4 bedrooms

Fully equipped house with barbeque, jacuzzi & patio | Mountain view

Oakland, West Oakland, Maryland, United States
from $687
per night
from $687
per night
View deal
House Oakland
House ∙ 6 guests ∙ 2 bedrooms

House with barbeque & terrace

Oakland, West Oakland, Maryland, United States
from $278
per night
Good(6 ratings)
from $278
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
from $411
per night
Excellent(8 ratings)
from $411
per night
View deal
Lodge Oakland
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
from $234
per night
from $234
per night
View deal
Lodge Oakland
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with garden

Oakland, West Oakland, Maryland, United States
from $234
per night
from $234
per night
View deal
Lodge Oakland
Lodge ∙ 2 guests ∙ 1 bedroom

Nice lodge with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
from $248
per night
from $248
per night
View deal
Lodge Oakland
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 room for 2 persons

Oakland, West Oakland, Maryland, United States
from $234
per night
from $234
per night
View deal
Motel Oakland
Motel ∙ 2 guests ∙ 1 bedroom

Motel

Oakland, West Oakland, Maryland, United States
from $135
per night
from $135
per night
View deal
Motel Oakland
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 persons

Oakland, West Oakland, Maryland, United States
from $133
per night
from $133
per night
View deal
Motel Oakland
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 persons

Oakland, West Oakland, Maryland, United States
from $118
per night
Outstanding
from $118
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
from $262
per night
Outstanding(34 ratings)
from $262
per night
View deal
House Oakland
House ∙ 15 guests ∙ 4 bedrooms

Family-friendly house with patio, jacuzzi & grill

Oakland, West Oakland, Maryland, United States
from $673
per night
Outstanding(9 ratings)
from $673
per night
View deal
House Oakland
House ∙ 9 guests ∙ 4 bedrooms

House | Pet-friendly

Oakland, West Oakland, Maryland, United States
from $102
per night
from $102
per night
View deal

Vacation Rentals With Fireplaces

Lodge Oakland
from $220
per night
Lodge ∙ 2 guests ∙ 1 bedroom

Charming lodge with garden

Oakland, West Oakland, Maryland, United States
Fireplace
View deal
House Oakland
from $284
per night
House ∙ 9 guests ∙ 5 bedrooms

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

5.0
Outstanding(34 ratings)
Oakland, West Oakland, Maryland, United States
Fireplace
View deal
House Oakland
from $363
per night
House ∙ 9 guests ∙ 3 bedrooms

Vacation home with jacuzzi & BBQ

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

Budget-friendly Vacation Rentals in Oakland

Find Fantastic yet Inexpensive Offers

House Oakland
from $251
per night
House ∙ 11 guests ∙ 3 bedrooms

Child-friendly house

Oakland, West Oakland, Maryland, United States
View deal
Bed and breakfast Oakland
from $142
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with barbecue | Suitable for remote work

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 $817
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 $325
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 $674
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 $863
per night
HomeToGo
House ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent(12 ratings)
Oakland, West Oakland, Maryland, United States
View deal
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Popular Rental Amenities in Oakland

  • Pet-friendly (8)
  • WiFi (31)
  • Fireplace (18)
  • Air conditioning (24)
  • Hot tub (10)
  • TV (23)
  • Kitchen (18)
  • Grill (10)
  • No pets (23)
  • Fishing (6)
  • 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, $444 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).

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 28 rentals
🌙 Nightly prices starting at $113
⭐ Popular amenities Pets allowed, Internet and Fireplace
🐾 Pet friendly homes 8 homes
21 reviews
Oakland vacation rentals have an average rating of 4.5/5 on 21 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 $113 per night. Average prices for house rentals are $498 per night. Cabins in Oakland cost $942 per night on average.

How many vacation homes are available to book in Oakland?

There are 28 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 $444.

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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