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Find Extended Stay Hotels in Oakland, MD

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Top Oakland Extended Stay Hotels | Reserve now, pay later

WiFi, bed sheets
Couples Retreat: The HayLoft- Rustic Escape For 2
Couples Retreat: The HayLoft- Rustic Escape For 2
10.0 out of 10, Exceptional, (5)
"Peggy was wonderful and the hayloft was great! "
$207 nightly
The price is $234
Oct 16 - Oct 17
Total with taxes and fees
Couples Retreat: The HayLoft- Rustic Escape For 2
WiFi, bed sheets
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
10.0 out of 10, Exceptional, (8)
"We had an awesome stay here! The yurt was absolutely beautiful, and the location was perfect. We would 100% stay again"
$205 nightly
The price is $232
Oct 23 - Oct 24
Total with taxes and fees
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Exterior
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
10.0 out of 10, Exceptional, (3)
"The place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
$311 nightly
The price is $352
Nov 3 - Nov 4
Total with taxes and fees
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Property grounds
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
2.0 star property
10.0 out of 10, Exceptional, (8)
"Nothing negative to say. Beautiful place and friendly owner. Owner is accessible and very accommodating. "
$651 nightly
The price is $736
Oct 27 - Oct 28
Total with taxes and fees
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Property grounds
“Moonbeam” (Airstream)
“Moonbeam” (Airstream)
10.0 out of 10, Exceptional, (3)
"Moonbeam was nice and outdoor space was awesome. We walked the trail and had dinner in Deep Creek.. Highly recommend "
$196 nightly
The price is $222
Oct 16 - Oct 17
Total with taxes and fees
“Moonbeam” (Airstream)
Terrace/patio
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
10.0 out of 10, Exceptional, (31)
"We LOVED the house! Clean, cozy, great little town. Couldn’t ask for better hosts!"
$517 nightly
The price is $585
Oct 22 - Oct 23
Total with taxes and fees
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
Fridge, microwave, oven, stovetop
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
10.0 out of 10, Exceptional, (1)
"Wonderful place for the perfect getaway! Just like the photos definitely worth every penny. Just have in mind that you are in the woods so the bugs are inevitable but the inside of the place was very clean.Me and my family took advantage of all the amenities from the grill, hot tub, fire place. Don't think twice and book this place!"
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Terrace/patio
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
10.0 out of 10, Exceptional, (16)
"We rented "
$653 nightly
The price is $692
Oct 29 - Oct 30
Total with taxes and fees
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
Smart TV, video games
In the heart of Deep Creek Lake! - "Shamrock Inn"
In the heart of Deep Creek Lake! - "Shamrock Inn"
9.6 out of 10, Exceptional, (5)
"Place was absolutely gorgeous host was very accommodating. Can't say enough good things about it"
$442 nightly
The price is $469
Oct 21 - Oct 22
Total with taxes and fees
In the heart of Deep Creek Lake! - "Shamrock Inn"
Fridge, microwave, oven, stovetop
That Special Place
That Special Place
10.0 out of 10, Exceptional, (26)
"We had a great stay. Everything was clean and very nice. Weather was rainy but still plenty of things to do inside. Great location and close to many activities indoors and outdoors. "
$410 nightly
The price is $435
Nov 2 - Nov 3
Total with taxes and fees
That Special Place
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.
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Find out more about Oakland

Discover top Oakland attractions

Oakland, Maryland, is a paradise of adventure and relaxation for travelers. Begin your journey at Deep Creek Lake, where families can enjoy a variety of water sports in the summer, including paddleboarding and jet skiing, or cozy up by a fire as the autumn leaves create a stunning backdrop. For those who appreciate history, the Garrett County Historical Museum offers engaging exhibits that bring the local past to life, perfect for a family outing. Nature enthusiasts will find solace at Swallow Falls State Park, where you can hike scenic trails leading to breathtaking waterfalls and lush forests, ideal for a family picnic. Don’t miss the chance to visit the Wisp Resort, where year-round activities range from skiing and snowboarding in winter to mountain biking in summer, ensuring adrenaline-filled days. When it comes to accommodations, the area around Deep Creek Lake offers charming lodges and upscale hotels with stunning lake views, allowing you to unwind after a day of exploration. Enjoy attentive service and comfortable amenities as you relax and plan tomorrow’s adventures, all while taking in the beauty of your surroundings.

Find the best extended stay hotels in Oakland

For travelers seeking accommodations with kitchen facilities in Oakland, Maryland, these top hotel options provide everything you need for a comfortable and convenient stay, complete with essential cooking amenities.

Suites at Silver Tree A213: Studio Suite with Lake View, Sleeps 4, Cozy Fireplace

  • Why it's great for an extended stay: Rated 9.4, this studio suite offers a well-appointed kitchenette featuring a refrigerator, microwave, and dishwasher, making it ideal for guests who love to cook. The enchanting lake view and cozy fireplace create a welcoming place for relaxing after a day of adventure.
  • Other amenities: Guests can indulge in a variety of nearby activities such as paddleboating and golfing, with options for hiking and winery tours. The suite includes a balcony for enjoying the view, as well as a dining table for shared meals. With additional features like parking, fitness facilities, and water sports available nearby, this suite is perfect for making the most of your stay.
  • Nearby attractions: Deep Creek Lake - 0.68 miles, Mount Nebo Wildlife Management Area - 4.64 miles, Deep Creek Lake State Park - 2.35 miles

Expand your search

Most booked related extended stays in Oakland in 2025

Oakland apart-hotels
Apart-hotels for extended stays
Apart-hotels for extended stays
Oakland vacation homes with a kitchen
Vacation homes with a kitchen
Vacation homes with a kitchen

Frequently asked questions

What are the best long-term hotels in Oakland?
If you're considering an extended stay in Oakland, you'll need someplace loaded with amenities. One of our favorites? Schmidt Lodge 3 Bedroom House. It comes with a barbecue grill, fitness facilities and a kitchen for you to experiment with local market finds. Another long-term hotel to look into is Largest Rental Estate In Md Private Indoor Pool. With conveniences such as a nearby laundromat, a swimming pool and kitchen facilities, a stay here is nice and comfortable.
What are the best weekly hotel rentals in Oakland?
Lakefront cabins with weekly rates, airport hotels perfect for overnighters, city apartments suited to both short and long stays — whatever you're after, Expedia will have your ideal match. Lake Access Home With A/c, Wood Fireplace And Outdoor Fire Pit is one of the top long-term hotels in Oakland. If features lots of great amenities, from a kitchen to a sofa bed and a nearby laundromat. Beautiful Lake Access Home With Dock Slip And Outdoor Hot Tub is also worth considering. Spend your break here and you'll have access to a nearby coin laundry and a nearby laundromat. To see some featured 7-day deals, or build your own, head to Expedia's One-week Vacations & Getaways page.
What are the top pet-friendly extended stay hotels in Oakland?
Your best bud doesn't have to feel left out when you go on vacation. Spend your extended stay in Oakland at Dogs Welcome Lakefront Home W. This pet-friendly property comes with conveniences such as pet-friendly services and a washing machine. Dogs Welcome Beautiful Lake Area Home W will also lay out the welcome mat for your precious pup. It features pet-friendly services, on-site parking options and more.
What are the best extended stay hotels with kitchens in Oakland?
Do some sightseeing and then head back and whip up a delicious homestyle meal at Lake Area Home With Hot Tub, Pool Table. Featuring a kitchen, a fireplace and a king bed, it has amenities that are made for a long-term stay with the family. Schmidt Lodge 3 Bedroom House is another top property with a kitchen. Enjoy the use of a fireplace, a barbecue grill and more during your visit to Oakland.
Can I find extended stay hotels with pools in Oakland?
Whether you're the type of person who wants to do laps or just watch life float by, a pool is a fantastic addition to any getaway. Build memories with your friends or family at Lakefront Home With Swimming Area. This extended stay in Oakland also has a washing machine and a patio. After a day of sightseeing, relax poolside at Dogs Welcome Lakefront Home W. This is another traveler favorite that features a nearby laundromat and a queen bed.Oakland has an oceanic climate and temperatures range between 57 ºF and 78 ºF in the summer months. If you'd love to spend most of your escape splashing around in the water, this is a fabulous time to visit.
What are the top extended stay hotels with 2 bedrooms in Oakland?
Dogs Welcome Lakefront Home W is a popular option for long-term stays in Oakland. Along with two bedrooms, it comes with plenty of amenities including a sofa bed and an oven. You'll also be comfy at Lake Area Home With Gas Fireplace. Put your suitcases down here and make use of a queen bed and a washing machine. Whether you're vacationing with family or friends or you just want more space to spread out, you'll appreciate that extra bedroom.
Why book an extended stay hotel in Oakland through Expedia?
Lock in your extended stay hotel in Oakland with Expedia and get access to the best properties at the lowest prices around. Along with our terrific offers and reward programs, we make finding the perfect long-term stay a piece of cake. Use our filter tool to search for properties according to location, ratings, nearby attractions and more. Some long-term rentals may offer weekly rates to help keep more dollars in your pocket. Usually equipped with essential amenities like a refrigerator and dining area, your next extended stay in Oakland is only a couple of clicks away!
What can I expect from an extended stay hotel?
Save your hard-earned money and enjoy comfort and convenience with an extended stay hotel in Oakland. Whether you'd like a cozy studio for yourself or a spacious option that'll fit your entire crew, these types of properties provide amenities that'll make you feel at home. Along with standard conveniences like a bar and a pool, many extended stay hotels have kitchens and a washer and dryer. This means you can make your own tasty meals and wash your own clothes, allowing you to keep a little jingle in your pocket. Weekly rates can help you save even more.

Top Oakland Hotel Reviews

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