Holiday Rentals in Oakland

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Our top choices for Oakland holiday rentals

10.0 out of 10, Exceptional, (192 reviews)
"Excellent property and great location "
United States
Eric P.
The price is €247
includes taxes & fees
25 Jan - 26 Jan
Handcrafted Riverfront Cabin on 10 acres

Cottage in Pleasant Mount

Equestrian House Suites
3.0 star property
The price is €524
includes taxes & fees
23 Jan - 24 Jan
Equestrian House Suites
8.8 out of 10, Excellent, (23 reviews)
"Our family had a lovely time on this charming home. From someone who grew up in the Catskills, this was a wonderful getaway from the usual hustle & bustle life."
United States
Liza G.
The price is €269
includes taxes & fees
25 Jan - 26 Jan
Charming 120-year-old farmhouse by the creek
10.0 out of 10, Exceptional, (12 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is €177
includes taxes & fees
26 Jan - 27 Jan
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
The price is €254
includes taxes & fees
2 Feb - 3 Feb
Vacation Cottage Getaway • Close to Ski Mountain
The price is €258
includes taxes & fees
25 Jan - 26 Jan
The Hideout Cottage • Near Camps & ELK Ski
9.8 out of 10, Exceptional, (39 reviews)
"We had a lovely stay. The mountain and valley views from the cabin were spectacular. The property was beautifully landscaped and maintained. "
United States
duane r.
The price is €177
includes taxes & fees
29 Jan - 30 Jan
King Cabin Secluded Romantic Space Near Elk Mountain. Hot Tub, Firepit & Views!
9.0 out of 10, Wonderful, (2 reviews)
"Would've liked to have more to cook with than just a microwave, other than that the stay was commendable."
United States
Jeremy
The price is €319
includes taxes & fees
23 Jan - 24 Jan
2BR Premium Duplex • Close to Ski Adventures
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"the stay was fine, never knew there was a heated pool"
United States
Aliyah A.
The price is €498
includes taxes & fees
2 Feb - 3 Feb
Forest Hideout Cottage • Nature Haven Close to Ski Adventures
The price is €195
includes taxes & fees
23 Jan - 24 Jan
Deluxe Duplex • Near Camps & ELK Ski
10.0 out of 10, Exceptional, (11 reviews)
"Perfect place to bring the family for a quiet ski holiday. "
United States
Pamela S.
The price is €244
includes taxes & fees
26 Jan - 27 Jan
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Lakefront! Hot Tub-Sauna-Cold Tubs-SUPs-Bikes-Canoe-Kayak-Sundeck-Firepit-Dock!
9.8 out of 10, Exceptional, (67 reviews)
"The house was perfect for our weekend. We appreciated that it was spotless and that the beds were super comfortable. Thank you! "
United States
Ronni
The price is €273
includes taxes & fees
23 Jan - 24 Jan
Waterfront Properties vacation rental
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location, clean, host was very helpful answering questions about the property / surrounding area."
United States
Kiel P.
The price is €336
includes taxes & fees
23 Jan - 24 Jan
Ska'no'ne - WINTER BEAUTY. Skiing, Ice Skating all within a short drive,
10.0 out of 10, Exceptional, (15 reviews)
"A couple of our crew stayed here for the last couple weeks while out of town working on a job, and the cabin felt like home, it was clean, the host was super responsive, and it was just the perfect place for us. "
United States
RHL C.
The price is €306
includes taxes & fees
23 Jan - 24 Jan
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
9.6 out of 10, Exceptional, (7 reviews)
"We enjoyed the weekend getaway with family. The house was very cozy and the hostess was very kind. Thank you very much. "
United States
Rosa P.
The price is €310
includes taxes & fees
25 Jan - 26 Jan
Angler and Nature's delight - West Branch Delaware
10.0 out of 10, Exceptional, (92 reviews)
"Beautiful place. We really enjoyed out stay."
United States
Tom B.
The price is €166
includes taxes & fees
23 Jan - 24 Jan
Quiet Lakefront Retreat nestled in the woods.

Holiday Home in Hancock

Hale Eddy
2.0 star property
The price is €273
includes taxes & fees
25 Jan - 26 Jan
Hale Eddy
The price is €451
includes taxes & fees
23 Jan - 24 Jan
Rustic Cabin - Lakewood Lodge
The price is €634
includes taxes & fees
8 Feb - 9 Feb
Relaxing • Rejuvenation • Perfect Stay Close to Ski Slopes
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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Top Oakland Hotel Reviews

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as €177 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakland has to offer?

Mountain Views, Private Pond, Mins 2 Elk Mountain: This holiday home rental outside of Oakland is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Oakland?

Explore the area and family-friendly sights such as Animal Adventure Park, or get out into nature at a spot like Susquehanna River. In the wider area, you’ll find Heart Lake and Shehawken Lake.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.