Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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Guest favorite

Cabin in Vernon Township

4.96 out of 5 average rating, 138 reviews

Mountain Creek Views Guest Suite

Guest suite/private side entry. Host lives upstairs. If you would like to have the host absent, there is a fee of $40 per night. Escape to our modern mountain retreat with breathtaking views and easy access to outdoor adventures - 2min to the Appalachian Trail - 8min to Mountain Creek - 10min to Warwick drive-in movie theatre - Hiking trails all over And when you're ready to relax, you'll have a comfortable and inviting space to call home. We take pride in providing exceptional hospitality.

Sep 2 – 9

G$26,213 GYD per night

Guest favorite

Cabin in Greenwood Lake

4.93 out of 5 average rating, 177 reviews

Lakeview Cabin at Greenwood Lake

A cozy cabin with modern amenities including new furnishings, appliances, internet, wifi, and television. Enjoy open plan living and dining room with connected full kitchen; queen bedroom; office, and a bath with walk-in shower. A large wrap-around deck with gas grill and lots of seating overlooks the lake. Parking for two vehicles. Five minutes from the Village of Greenwood Lake, 15 minutes from the Village of Warwick, and surrounded by recreation, food, shops, and more. On the NY/NJ bus line.

Mar 12 – 19

G$41,793 GYD per night

Guest favorite

Guest suite in Chester

4.95 out of 5 average rating, 230 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Jun 15 – 22

G$22,188 GYD per night

Guest favorite

Guest suite in Pequannock Township

4.92 out of 5 average rating, 105 reviews

Comfortable & Private Guest Suite

Private home with a guest space on the 2nd story. Located in a quiet residential area with on and off street parking. Suite has a private entrance outdoor seating, personal door key code. Its a 1 bed room with a king bed , living room has a couch w/2 recliners. Access to washer & dryer in common area. Centrally located & 30 min to1 hr to major Airports, NY, Penn, NJ beaches and ski resort. Close to restaurants , shopping . Access to public transportation via bus and train is within minutes.

Jun 4 – 11

G$24,789 GYD per night

Guest favorite

Cabin in Greenwood Lake

4.96 out of 5 average rating, 386 reviews

"Cabinessence" on Greenwood Lake, 60 mi from NYC

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Sep 16 – 23

G$46,426 GYD per night

Guest favorite

Cabin in West Milford

4.98 out of 5 average rating, 108 reviews

Peaceful Lake Front Log Cabin w/3 bedrooms up to 7

Enjoy this peaceful lake front log cabin all to yourself and 6 more of family or friends! Sleeps 7. We are located just an hour from NYC. The cabin has recently been refinished with a new kitchen, appliances and all new furniture. Relax in our Lake front yard where you'll find a seating area with a firepit, large table for all your sunset dinners, a 2 person Hammock and a large BBQ. The cabin's location to many seasonal activities and events makes this an ideal year round destination!

Nov 23 – 30

G$87,161 GYD per night

Guest favorite

Cottage in Greenwood Lake

4.97 out of 5 average rating, 279 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #32370

Jan 1 – 8

G$70,161 GYD per night

Guest favorite

Apartment in Fair Lawn

4.88 out of 5 average rating, 349 reviews

Fair Lawn 1bedrm apt ,wi-fi ,TV,kitch,parking,ent

Fully furnished 1 bedroom apt. with Qn size bed, European kitchen, bath, private parking, entrance, bedroom/living room, dining. Queen size Aerobed for additional guests. Fastest 5G/400MBps Wi-Fi, cable TV, + Netflix, Showtime. The kitchen/dining room has Tyent ACE-11 water system, refrigerator (water and ice), microwave, large countertop toaster oven, coffee maker, dishwasher, and other appliances. Great for couples, solo adventurers, business travelers, or small families.

Oct 1 – 8

G$20,899 GYD per night

Guest favorite

Apartment in Suffern

4.95 out of 5 average rating, 103 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

Jul 7 – 14

G$33,656 GYD per night

Guest favorite

Apartment in Little Falls

4.91 out of 5 average rating, 143 reviews

Suburban NYC; Private, clean apt. own entrance

Family Friendly, private walkout basement apartment with private entrance in a quiet neighborhood. Special rates for Health Care Workers and Long term rentals. Please inquire. The apartment is newly constructed, full of light and 1400 square feet. Perfect for a working professional or a family. Nice shared patio and large backyard to relax in. Kitchen is brand new with counters and appliances. Equipped with countertop oven and induction cooktop.

Oct 10 – 17

G$24,088 GYD per night

Guest favorite

Apartment in Prospect Park

4.85 out of 5 average rating, 150 reviews

Modern Apt, Parking & Own Patio 30 min to NYC

A Cozy space minimalist Smoke and Pet Free entire apartment with luxury finishes.Perfect for quiet minimalist travelers . First floor apartment of a lovely multi family home in a quiet neighborhood . Perfect for relaxation or a work trip. Your own patio & Parking. This apartment is not for smokers, if you are a smoker please do not book. This apartment is fully equipped with all the toiletries and extra linen one would need. We do not allow animals.

Jan 5 – 12

G$27,049 GYD per night

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Jan 12 – 19

G$17,628 GYD per night