Oakland Vacation Packages 2026 from $525

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Your Oakland Vacation

When a fun city break is calling, answer it with a vacation package to Oakland. The neighborhood of Blakeslee, which is great for nature, watersports and views, makes a wonderful base for your adventures. If going to see the sights is a priority during your trip to Oakland, be sure to swing by popular attractions like Swallow Falls State Park and Herrington Manor State Park. No matter your travel plans or the size of your budget, putting together a tailored Oakland vacation is a cinch with Expedia.

The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.

Sonesta Essential Fairmont

$525

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Morgantown (MGW)

8/10 Very Good! (1,004 reviews)

Lakeview Golf Resort

$589

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Morgantown (MGW)

6.4/10 (965 reviews)

Outdated! Had to change rooms, toilet missing attachment to plunger, both bed dipped in middle, and ceiling was so low in the bathroom that I scratched my knuckles on the popcorn ceiling when I took off my shirt. Switched rooms and the only difference was the toilet worked.

Reviewed on Aug 17, 2026

Modern Homestead Guest House

$581

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Morgantown (MGW)

9/10 Wonderful! (46 reviews)

Very cute and sweet place.

Reviewed on Jul 8, 2026

Candlewood Suites MORGANTOWN-UNIV WEST VIRGINIA by IHG

$621

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Morgantown (MGW)

9.2/10 Wonderful! (689 reviews)

Ok, so this is a bit of strange review. The hotel was nice, so were the staff …. BUT, while staying there, my daughter went to bathroom and grabbed a towel to dry off her face. The towel was neatly folded with 4 or 5 others, but when she lifted it and took a look, it had brown stains on it. No joke, she thought they might be chocolate and called my wife over … they were NOT chocolate. There were other cleanliness issues as well, though minor in comparison to feces on your towel. When I reached out, everyone was very apologetic, but literally no compensation or action taken. As I prefer feces-less towels, will be avoiding IHG run facilities in future.

Reviewed on Aug 5, 2026

Hampton Inn & Suites Morgantown / University Town Centre

$738

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Morgantown (MGW)

9.4/10 Exceptional! (943 reviews)

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Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland

A waterfall cascading over rocks into a clear pool.

Mountainside

Mountainside might not have many top sights, but Deep Creek Lake and Deep Creek Lake State Park are two attractions nearby that you can check out.

Blakeslee

While there might not be top attractions in Blakeslee, you can explore the larger area and discover places like Deep Creek Lake and Thousand Acres Lakeside Golf Course.

A river winding through a densely forested area with a small town and a lake.

Paradise Point

If you're looking for some top things to see and do in Paradise Point and surrounding area, you can visit Deep Creek Lake and Deep Creek Lake State Park.

Silver Ridge

While Silver Ridge isn't home to many top sights, Deep Creek Lake and Deep Creek Lake State Park are some notable places to visit nearby.

The View

While there might not be top attractions in The View, you can explore the larger area and discover places like Deep Creek Lake and Deep Creek Lake State Park.

Stay near popular Oakland attractions

A waterfall cascading over a rocky cliff surrounded by lush greenery.

Swallow Falls State Park

9.8/10 (138 reviews)

Maryland's highest free-falling waterfall cascades 53 feet at Swallow Falls State Park. Wander through ancient hemlock forests and listen to the soothing rush of water along well-maintained trails.

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A log cabin with a stone chimney, surrounded by snow-covered ground and trees.

Herrington Manor State Park

9.4/10 (12 reviews)

Nestled in Garrett County, Herrington Manor State Park features a pristine 53-acre lake for swimming, boating, and fishing. Reserve one of the 20 furnished log cabins for a woodland retreat with access to scenic trails.

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Lower Deep Creek Heritage Conservation Fund Site

This 106.5-acre park offers tranquil trails through lush Maryland landscapes for both leisurely strolls and challenging hikes. Explore diverse ecosystems and seasonal beauty with comfortable shoes and water in hand.

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Mount Nebo Wildlife Management Area

You can take time to visit Mount Nebo Wildlife Management Area during your travels to Oakland. While you're in the area, stroll along the lakeside.

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Broadford Park

Nestled around a scenic lake in Oakland, Broadford Park offers family-friendly swimming, boating, and trails. Rent a kayak for a peaceful afternoon or reserve a pavilion for a premium lakeside picnic experience.

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Glades Park

After visiting Glades Park, make a plan to see the other sights and activities in Oakland. While you're in the area, stroll along the lakeside.

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Ruth Enlow Library of Garrett County

The Ruth Enlow Library has served as Oakland's literary hub since 1915, offering resources and community programs. Browse the diverse collection or join their seasonal reading events in this welcoming space.

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Mountain Lake Park Town Hall

This historic town hall stands as a testament to Mountain Lake Park's Victorian resort past. Visit during the annual Chautauqua celebration to experience performances and lectures in an authentic setting.

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Oakland Hotel Deals

Baja Motel

1501 Maryland Hwy Oakland MD

Fully refundableReserve now, pay when you stay

$102 nightly

$116 total

Aug 31 - Sep 1

Total with taxes and fees

9/10 Wonderful! (119 reviews)

"Easy chexk i. And oit, friendly staff and nice rooms . Really good reataurant on site to boot"

Reviewed on Aug 17, 2026

The Garrett Inn

17848 Garrett Highway Oakland MD

$126 nightly

$144 total

Aug 20 - Aug 21

Total with taxes and fees

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Oakland MD

9.6/10 Exceptional! (22 reviews)

"We had a great week. The home is well cared for and comfortable. The bedrooms were a nice size. We relaxed in the hot tub, while enjoying a view of the lake. The location allowed us to explore Deep Creek, Accident, Oakland, Frostburgh and West Virginia. The owner responded promptly to all of our ..."

Reviewed on Aug 16, 2026

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See all 802 properties in Oakland

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Oakland Vacation Packages

Things to do in and around Oakland

Oakland, Maryland, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore the scenic beauty of the area, enjoy various outdoor adventures, and take advantage of recreational activities. Popular attractions include local ski resorts and vibrant nightlife options, ensuring there’s something for everyone to enjoy during their stay in this charming town.

Shopping

In Oakland, you can visit local shops like the Oakland Antique Mall for unique finds and handmade crafts. If you're up for a drive, head to the nearby Deep Creek Lake area, where you'll find the Wisp Resort's shops and local boutiques offering a variety of gifts and souvenirs.

Recreation

Explore Swallow Falls State Park for serene hikes among breathtaking waterfalls and lush forests, perfect for relaxation and rejuvenation. Enjoy a round at Lodestone Golf Club, where stunning mountain views meet challenging greens, blending sports with the great outdoors. Experience the cultural charm at Music at Penn Alps, featuring live performances in a cozy theater setting.

Adventure

Experience the thrill of skiing at Wisp Resort, located 11 miles from Oakland, where you can carve through snowy slopes. For water adventures, head to Adventure Sports Center International, 10 miles away, for exciting water sports. Enjoy family-friendly fun at Funland, also 11 miles from Oakland, with arcade games galore.

Nightlife

Oakland's nightlife offers a cozy atmosphere with local bars and live music. Check out the MoonShadow Café for great food and entertainment. For a laid-back vibe, visit the Deep Creek Brewing Company, where you can enjoy craft beers and often catch live performances from talented musicians.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Oakland

Oakland, Maryland, is perfect for outdoor enthusiasts and those seeking a romantic getaway. Visitors can explore beautiful lakes, national parks, and nature reserves, making it ideal for family adventures. Don’t miss local attractions like the Oakland Zoo, Oakland Museum, and Oakland Arena for an engaging experience in this charming town.

Deep Creek Lake: Experience the serene beauty of Deep Creek Lake, a stunning destination perfect for beach outings and romantic sunsets. The lake offers a variety of outdoor activities, from swimming and fishing to kayaking, all set against picturesque scenery that invites relaxation and adventure.
Cathedral State Park: Immerse yourself in the natural wonders of Cathedral State Park, where adventure awaits amidst towering trees and scenic trails. Ideal for hiking and exploring, this park offers a peaceful retreat with opportunities to connect with nature in a breathtaking outdoor setting.
Thousand Acres Lakeside Golf Course: Enjoy family-friendly fun at Thousand Acres Lakeside Golf Course, where golf enthusiasts of all ages can play on a beautifully maintained course. The welcoming atmosphere and stunning lakeside views make it a perfect spot for a day of recreation and quality family time.

Best time to go to Oakland

The best time to visit Oakland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	26.4°F (-3.1°C)	Light Rain	Mostly Cloudy	Average	Average
February	30.0°F (-1.1°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
March	37.6°F (3.1°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	47.7°F (8.7°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	57.6°F (14.2°C)	Light Rain	Mostly Cloudy	Average	Average
June	64.9°F (18.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	69.1°F (20.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	61.5°F (16.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	50.7°F (10.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
November	39.0°F (3.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	32.5°F (0.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High

Tips to save on your trip to Oakland

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Oakland.
Consider traveling to Oakland during the low season (March to April and October) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Oakland Essential Information

Language	English
Currency	U.S dollars
Population	1,900
Max Temp Winter	35ºF
Max Temp Summer	80ºF
Top Sights	Herrington Manor State Park, Wolf Den Run State Park and Swallow Falls State Park

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Frequently asked questions

How much does an Oakland vacation package cost?

You'll find cheap prices from $525 on Expedia for your Oakland getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Oakland costs.

What are the cheapest months to go to Oakland?

If you're hoping to book a cheap Oakland vacation package, consider traveling in July, August and December. You're likely to find better rates on airfares and hotels during these months — perfect for a budget-friendly getaway.

How many days is enough for Oakland?

Usually, a handful of days is enough to tick off the major attractions during your Oakland vacation. But if you'd like to have time to unwind or go on day tours, consider extending your trip.

How to find the best Oakland package deals?

Finding a cheap Oakland package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Oakland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.

Is it cheaper to book an Oakland vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can tailor your Oakland escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.

When to book a vacation package to Oakland?

If you've got your Oakland vacation dates locked in, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.

Does Expedia offer Book Now, Pay Later Oakland vacation packages?

Your Oakland break is meant to be an escape from your daily routine, not a source of money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Oakland Vacations from $525

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Oakland Vacation

The Latest Oakland vacation packages

Sonesta Essential Fairmont

Lakeview Golf Resort

Modern Homestead Guest House

Candlewood Suites MORGANTOWN-UNIV WEST VIRGINIA by IHG

Hampton Inn & Suites Morgantown / University Town Centre

Where to stay in Oakland

Mountainside

Blakeslee

Paradise Point

Silver Ridge

The View

Stay near popular Oakland attractions

Swallow Falls State Park

Herrington Manor State Park

Lower Deep Creek Heritage Conservation Fund Site

Mount Nebo Wildlife Management Area

Broadford Park

Glades Park

Ruth Enlow Library of Garrett County

Mountain Lake Park Town Hall

Oakland Hotel Deals

Baja Motel

The Garrett Inn

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Find the Best Oakland Vacation Packages

Things to do in and around Oakland

Find the best attractions near Oakland

Best time to go to Oakland

Tips to save on your trip to Oakland

Oakland Essential Information

More vacations you might like

Frequently asked questions

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