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

Vacation rentals in Oakland

Browse 23 available vacation homes and compared across 10 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

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

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

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

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 $273
per night
Good(7 ratings)
from $273
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 $451
per night
Excellent(8 ratings)
from $451
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 $140
per night
Outstanding(2 ratings)
from $140
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 $161
per night
Outstanding(6 ratings)
from $161
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 $283
per night
from $283
per night
View deal
Cabin Oakland
Cabin ∙ 4 guests ∙ 1 bedroom

Family-oriented wonderful cabin with barbecue, yard & terrace | Pets allowed

Oakland, West Oakland, Maryland, United States
This cozy cabin in Garrett County features a fireplace, yard, and pet-friendly space, perfect for a family getaway.
from $134
per night
from $134
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
This waterfront house rental in Deer Park features a hot tub, balcony, and mountain views, perfect for gatherings of 12.
from $627
per night
from $627
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 $129
per night
Outstanding(14 ratings)
from $129
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 $307
per night
Excellent(17 ratings)
from $307
per night
View deal
Apartment Oakland
Apartment ∙ 8 guests ∙ 3 bedrooms

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

Oakland, West Oakland, Maryland, United States
This waterfront apartment in Terra Alta features a pool, fireplace, kitchen, and mountain views, perfect for 8 guests.
from $203
per night
Outstanding(10 ratings)
from $203
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 $325
per night
Outstanding(11 ratings)
from $325
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 $371
per night
Excellent(25 ratings)
from $371
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 $670
per night
Outstanding(1 rating)
from $670
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(3 ratings)
from $299
per night
View deal
House Oakland
House ∙ 9 guests ∙ 3 bedrooms

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

Oakland, West Oakland, Maryland, United States
from $228
per night
Outstanding(26 ratings)
from $228
per night
View deal

Vacation houses with Balconies or Patios

House Oakland
from $332
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/Patio
View deal
Cabin Oakland
from $137
per night
Cabin ∙ 4 guests ∙ 1 bedroom

Cabin with patio & barbeque

Oakland, West Oakland, Maryland, United States
Balcony/Patio
View deal
Resort Oakland
from $190
per night
Resort ∙ 2 guests ∙ 1 bedroom

Holiday park with terrace & grill

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

Budget-friendly rental options

Enjoy affordable vacation rentals in Oakland offering exceptional value for money

Cabin Oakland
from $354
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?
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 $812
per night
House ∙ 18 guests ∙ 7 bedrooms
4.6
Excellent(21 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
4.3
Very good(31 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 $823
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 7 properties in Oakland allow you to bring your pet. In addition, pet-friendly accommodations in Oakland cost, on average, $469 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.

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 $128
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 7 homes
🏊 Vacation rentals with pools 2 homes
35 reviews
Oakland vacation rentals have an average rating of 4.5/5 on 35 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 $128. $936 is the average nightly price for house rentals in Oakland. Condos in Oakland cost $295 per night on average.

How many vacation rentals are available for booking in Oakland?

There are 23 vacation rentals from 12 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 - 30% of rentals allow pets.

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