Vacation Rentals in Oakland - HomeToGo base64Hash Vacation Rentals in Oakland - HomeToGo

Vacation Rentals in Oakland

Find 34 available house rentals from 12 partners
Anytime
1 guest
Anytime
1 guest

  • 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 $117 per night!

House Oakland
-26%
Feb 22 - Mar 1
House ∙ 14 guests ∙ 5 bedrooms

Fully Equipped Spacious House with Terrace & BBQ | Lake View | Dogs Allowed

Oakland, West Oakland, Maryland, United States
$581$417
per night
Outstanding(68 ratings)
$581$417
per night
View deal
House Oakland
-46%
May 24 - May 31
House ∙ 12 guests ∙ 4 bedrooms

Fully Equipped Pleasant Vacation Home with Jacuzzi, Yard & Barbecue | Water View | Pets Allowed

Oakland, West Oakland, Maryland, United States
$518$403
per night
$518$403
per night
View deal
Motel Oakland
Apr 5 - Apr 12
Free cancellation
Motel ∙ 4 guests ∙ 1 bedroom

Motel | Perfect for Remote Work

Oakland, West Oakland, Maryland, United States
$119
per night
$119
per night
View deal
Motel Oakland
Jan 25 - Feb 1
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 Persons

Oakland, West Oakland, Maryland, United States
$117
per night
Outstanding
$117
per night
View deal
House Oakland
-19%
Aug 18 - Aug 25
House ∙ 9 guests ∙ 5 bedrooms

Children-Friendly Ample House with Terrace, Grill & Garden | Pets Are Welcome

Oakland, West Oakland, Maryland, United States
$404$280
per night
Outstanding(35 ratings)
$404$280
per night
View deal
House Oakland
-48%
Jun 4 - Jun 11
House ∙ 15 guests ∙ 5 bedrooms

Family-Oriented Vacation Home with Patio & Barbeque

Oakland, West Oakland, Maryland, United States
$1,220$518
per night
Outstanding(7 ratings)
$1,220$518
per night
View deal
House Oakland
-22%
May 31 - Jun 7
House ∙ 12 guests ∙ 4 bedrooms

Family-Oriented Vacation Home with Patio | Mountain View | Pet-Friendly

Oakland, West Oakland, Maryland, United States
$476$346
per night
Excellent(23 ratings)
$476$346
per night
View deal
House Oakland
Jun 7 - Jun 14
House ∙ 15 guests ∙ 4 bedrooms

Child-Friendly Charming Vacation Home with Barbecue & Jacuzzi

Oakland, West Oakland, Maryland, United States
$520
per night
Outstanding
$520
per night
View deal
House Oakland
-65%
Apr 14 - Apr 21
Free cancellation
House ∙ 9 guests ∙ 3 bedrooms

Family-Friendly Pleasant House with Yard, Jacuzzi & Patio | Pets Allowed

Oakland, West Oakland, Maryland, United States
$618$261
per night
Outstanding(35 ratings)
$618$261
per night
View deal
House Oakland
House ∙ 14 guests ∙ 4 bedrooms

House with Terrace, BBQ & Yard | Lake View

Oakland, West Oakland, Maryland, United States
from $442
per night
Outstanding(9 ratings)
from $442
per night
View deal
House Oakland
-42%
Apr 12 - Apr 19
House ∙ 11 guests ∙ 3 bedrooms

House with Hot Tub, Grill & Terrace | Nature View

Oakland, West Oakland, Maryland, United States
$293$196
per night
$293$196
per night
View deal
Lodge Oakland
Jan 25 - Feb 1
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with Yard

Oakland, West Oakland, Maryland, United States
$229
per night
$229
per night
View deal
Lodge Oakland
Jan 25 - Feb 1
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 Room for 2 Persons

Oakland, West Oakland, Maryland, United States
$229
per night
$229
per night
View deal
Lodge Oakland
Jan 25 - Feb 1
Lodge ∙ 2 guests ∙ 1 bedroom

Lodge with 1 Room for 2 Persons

Oakland, West Oakland, Maryland, United States
$229
per night
$229
per night
View deal
Lodge Oakland
Jan 25 - Feb 1
Lodge ∙ 2 guests ∙ 1 bedroom

Lovely Lodge with 1 Room for 2 Persons

Oakland, West Oakland, Maryland, United States
$242
per night
$242
per night
View deal

Vacation Rentals With Fireplaces

House Oakland
Jul 19 - Jul 26
$558
per night
House ∙ 12 guests ∙ 6 bedrooms

Charming House | Pets Allowed

Oakland, West Oakland, Maryland, United States
Fireplace
View deal
House Oakland
Jul 19 - Jul 26
$315
per night
House ∙ 11 guests ∙ 3 bedrooms

House with 3 Rooms for 11 Persons

Oakland, West Oakland, Maryland, United States
Fireplace
View deal
House Oakland
Jul 19 - Jul 26
$284
per night
House ∙ 11 guests ∙ 4 bedrooms

Wonderful House with Terrace & Barbeque | Lake View | Pets Allowed

4.7
Excellent(3 ratings)
Oakland, West Oakland, Maryland, United States
Fireplace
View deal
See all offers

Best Vacation Home Deals in Oakland

Save up to 46%

House Oakland
Aug 29 - Sep 5
-46%
$644
$347
per night
House ∙ 15 guests ∙ 4 bedrooms

Child-Friendly Charming Vacation Home with Barbecue & Jacuzzi

5.0
Outstanding
Oakland, West Oakland, Maryland, United States
View deal

Search through the 34 properties featured in Oakland and find a welcoming accommodation for your vacation. All of the offers from the different providers are immediately compared by the search engine to help you save up to 46%.

Budget-friendly Vacation Rentals in Oakland

Find Fantastic yet Inexpensive Offers

House Oakland
Jul 19 - Jul 26
$284
per night
House ∙ 11 guests ∙ 4 bedrooms

Wonderful House with Terrace & Barbeque | Lake View | Pets Allowed

4.7
Excellent(3 ratings)
Oakland, West Oakland, Maryland, United States
View deal
House Oakland
Jul 19 - Jul 26
$558
per night
House ∙ 12 guests ∙ 6 bedrooms

Charming House | Pets Allowed

Oakland, West Oakland, Maryland, United States
View deal
House Oakland
Aug 9 - Aug 16
$315
per night
House ∙ 11 guests ∙ 3 bedrooms

House with 3 Rooms for 11 Persons

Oakland, West Oakland, Maryland, United States
View deal

Top-Rated Rentals and Accommodations in Oakland

Book Vacation Rental Offers with the Highest User Rating

Motel Oakland
Aug 9 - Aug 16
$142
per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 Persons

4.5
Excellent(50 ratings)
Oakland, West Oakland, Maryland, United States
View deal
Farmhouse Oakland
Jul 12 - Jul 19
$597
per night
Farmhouse ∙ 12 guests ∙ 6 bedrooms

Fully Equipped Farm with Yard, Sauna & Terrace

4.5
Excellent(8 ratings)
Oakland, West Oakland, Maryland, United States
View deal

Customer ratings and reviews

How are reviews collected?
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 $329
per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Oakland, West Oakland, Maryland, United States
View deal
from $329
per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Oakland, West Oakland, Maryland, United States
HomeToGo
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 $583
per night
HomeToGo
House ∙ 10 guests ∙ 5 bedrooms
4.9
Outstanding(7 ratings)
Oakland, West Oakland, Maryland, United States
View deal
from $583
per night
House ∙ 10 guests ∙ 5 bedrooms
4.9
Outstanding(7 ratings)
Oakland, West Oakland, Maryland, United States
HomeToGo
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 $641
per night
HomeToGo
House ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent(12 ratings)
Oakland, West Oakland, Maryland, United States
View deal
from $641
per night
House ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent(12 ratings)
Oakland, West Oakland, Maryland, United States
HomeToGo
View deal

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Popular Rental Amenities in Oakland

  • Pet-friendly (9)
  • WiFi (34)
  • Fireplace (19)
  • Air conditioning (27)
  • Hot tub (6)
  • TV (26)
  • Kitchen (24)
  • Grill (10)
  • No pets (25)
  • Fishing (4)
  • Balcony/patio (8)
  • Dishwasher (12)

Oakland is a perfect vacation spot for pet owners, as 9 properties in Oakland allow you to bring your pet. In addition, pet-friendly accommodations in Oakland cost, on average, $464 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 (11).

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 34 rentals
💳 Possible discounts up to 46%
🌙 Nightly prices starting at $117
⭐ Popular amenities Pets allowed, Internet and Fireplace
🐾 Pet friendly homes 9 homes
14,517 reviews
Oakland vacation rentals have an average rating of 4.4/5 on 14,517 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 $117 per night. Average prices for house rentals are $508 per night. Cabins in Oakland cost $942 per night on average.

How many vacation homes are available to book in Oakland?

There are 34 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 9 vacation rentals in Oakland that allow dogs , with an average nightly price of $464.

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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