Holiday Rentals in Oakland

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Holiday Rentals in Oakland

Cottage in Pleasant Mount

3.0 star property
The price is €527
includes taxes & fees
5 Dec - 6 Dec
Equestrian House Suites

Cabin in Starlight

10.0 out of 10, Exceptional, (182)
"Beautiful short stay at this wonderful property. "
United States
Arvin S.
The price is €264
includes taxes & fees
7 Dec - 8 Dec
Handcrafted Riverfront Cabin on 10 acres

Cottage in Hancock

8.8 out of 10, Excellent, (23)
"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 €275
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 120-year-old farmhouse by the creek

Cabin in Thompson

10.0 out of 10, Exceptional, (12)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is €178
includes taxes & fees
7 Dec - 8 Dec
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

Chalet in Lakewood

9.6 out of 10, Exceptional, (122)
"We loved the privacy and enjoyed all the kayaks, boat and canoe. Perfect lake vacation, plan on making it a yearly trip."
United States
CINDY M.
The price is €352
includes taxes & fees
6 Dec - 7 Dec
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

Cottage in Pleasant Mount

9.0 out of 10, Wonderful, (2)
"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 €330
includes taxes & fees
5 Dec - 6 Dec
2BR Premium Duplex • Autumn Midweek - 35% OFF Promo!

Cabin in Thompson

10.0 out of 10, Exceptional, (27)
"Very very beautiful sites and the hot tub was a must "
United States
Ethan F.
The price is €177
includes taxes & fees
22 Dec - 23 Dec
Queen Cabin Modern Cabin Near Skiing, Trails, Firepit, Hot Tub & Stargazing!

Holiday Home in Thompson

10.0 out of 10, Exceptional, (11)
"Perfect place to bring the family for a quiet ski holiday. "
United States
Pamela S.
The price is €253
includes taxes & fees
7 Dec - 8 Dec
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

Cottage in Montrose

10.0 out of 10, Exceptional, (90)
"My daughter and i really enjoyed our stay here. Kevin and tami made us feel at home and we loved swimming in the lake and all the nearby hiking options. We would stay here again!"
United States
Catherine W.
The price is €167
includes taxes & fees
7 Dec - 8 Dec
Quiet Lakefront Retreat nestled in the woods.

Holiday Home in Windsor

9.8 out of 10, Exceptional, (66)
"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 €279
includes taxes & fees
15 Dec - 16 Dec
Waterfront Properties vacation rental

Cabin in Deposit

10.0 out of 10, Exceptional, (13)
"Beautiful, clean, great care given to the details that make the stay special. The owner is wonderful."
United States
Anonymous traveller
The price is €308
includes taxes & fees
5 Dec - 6 Dec
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast

Cottage in Pleasant Mount

The price is €267
includes taxes & fees
9 Dec - 10 Dec
Vacation Cottage Getaway • Close to Camps • Autumn Midweek - 35% OFF Promo!

Apartment in Binghamton

9.4 out of 10, Exceptional, (3)
"Overall, my family had a nice stay at the apartment. The space was clean, comfortable with a modern vibe. The arcade game in the apartment was a plus. It’s convenient to some of the local dining options. It’s ideal for a family of four with the two bedrooms with double beds. It’s a walk up but the stairs are wide and easy to navigate. The owner was very responsive when we requested additional towels, and someone parked in the apartment’s designated spot (not his fault but was a little annoying,...
United States
William
Hip Dtwn Apt W/ Arcade & Gym

Holiday Home in Nineveh

10.0 out of 10, Exceptional, (3)
"Beautiful location, clean, host was very helpful answering questions about the property / surrounding area."
United States
Kiel P.
The price is €353
includes taxes & fees
5 Dec - 6 Dec
Ska'no'ne -Peaceful Living 1-bedroom house with central HVAC & WiFi on 13+ acres

Apartment in Binghamton

9.4 out of 10, Exceptional, (10)
"My daughter and I loved our weekend at the loft. The beds were very comfortable and the layout was perfect for what we needed. Lots of good food close by to walk to and we felt safe in the area. "
United States
ELIZABETH F.
The price is €217
includes taxes & fees
7 Dec - 8 Dec
Modern Urban Stay Dtwn Apt

Holiday Home in Union Dale

9.4 out of 10, Exceptional, (10)
"Great place!!"
United States
Linda H.
The price is €268
includes taxes & fees
2 Jan - 3 Jan 2026
Tioga Townhouse Xmas Holidays 20% Off Stay

Cottage in Pleasant Mount

The price is €266
includes taxes & fees
9 Dec - 10 Dec
The Hideout Cottage • Autumn Midweek - 35% OFF Promo!

Cottage in Pleasant Mount

2.0 star property
The price is €452
includes taxes & fees
5 Dec - 6 Dec
Countryside Retreat • Autumn Midweek - 35% OFF Promo!

Cottage in Hancock

The price is €482
includes taxes & fees
7 Dec - 8 Dec
Lakefront! Hot Tub-Sauna-Cold Tubs-SUPs-Bikes-Canoe-Kayak-Sundeck-Firepit-Dock!

Holiday Home in Hallstead

2.0 star property
9.0 out of 10, Wonderful, (9)
"We needed a place to stay for the 6 of us attending the funeral of our mother and this vintage home was the perfect place for us. It offered tranquil views which was just what we needed. "
United States
Paula M.
The price is €334
includes taxes & fees
31 Dec - 1 Jan 2026
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
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 €167 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 a lake, 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 Jimay's Flea Market and Heart 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.