Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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Guest favorite

Cottage in Greenwood Lake

4.93 out of 5 average rating, 168 reviews

Cozy home in the Village of Greenwood Lake

Adorable country retreat under an hour from NYC - perfect for a romantic couples getaway or a family of 4. Located in the village, our quaint cottage is walkable to everything; Restaurants, bars, grocer, cvs, bagels, bus stop and even the public beach!! Minutes away from TONS of local attractions; drive-in, skiing, renaissance fair, wineries, shopping, lake activities, orchards, creameries, parks, Appalachian trail, spa, rafting, golf, water park, & so much more. Pets welcome! Permit #21-07603

Guest favorite

Cabin in Vernon Township

4.96 out of 5 average rating, 170 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.

Guest favorite

Home in Greenwood Lake

4.98 out of 5 average rating, 101 reviews

Your lakefront castle awaits you …

Imagine a castle on a lake. Welcome to Castlebrook, a luxurious Lakefront home on Greenwood Lake, NY. This exquisitely appointed home has sweeping vistas of the lake yet is private enough for a relaxing getaway. 3 large bedrooms, 3 full baths, boat slip, jet ski dock, outdoor grill and firepit, meticulously manicured grounds await you just an hour from NYC, 15 minutes from Tuxedo train, 30 minutes from Legoland. Spacious entertaining areas, all with sweeping views of the lake. True luxury.

Guest favorite

Rental unit in Prospect Park

4.85 out of 5 average rating, 178 reviews

Modern NJ Apt, Parking & Own Patio 30 min to NYC

A sweet, simple retreat! This smoke-free, pet-free New Jersey apartment is perfect for minimalist travelers seeking peace. Great for unwinding or a work trip, it’s located on the first floor of a charming multi-family home in a quiet neighborhood. Enjoy your own patio and parking spot. Strictly no smoking—if you’re a smoker, please don’t book. Light cooking only, and no extra visitors or pets. Fully stocked with toiletries and linens, this cozy space is perfect for a low-key, easygoing stay!

Superhost

Cabin in Greenwood Lake

4.86 out of 5 average rating, 200 reviews

Get some R&R at the Rustic Retreat!

The Rustic Retreat is centrally located, 2 bedroom 1 bath cozy cottage is just what you've been looking for in this lake community. There is a 3-6 car driveway, newly renovated kitchen, open floor plan in the dining & living room, new shed bar/ fire pit, & sleeps 7 (Q in Master, F Sofa Bed Couch, T Bunk Beds, F Air Mattress). Located about 3 mins from Greenwood Lake and 10 mins from Warwick, many activities for your perfect getaway! IG @Rusticretreat22 Short Term Rental Permit # 21-0422

Guest favorite

Guest suite in Pequannock Township

4.93 out of 5 average rating, 121 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.

Guest favorite

Cabin in West Milford

4.99 out of 5 average rating, 146 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!

Guest favorite

Cabin in Greenwood Lake

4.92 out of 5 average rating, 226 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. Permit # 34312

Guest favorite

Cottage in Greenwood Lake

4.98 out of 5 average rating, 320 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

Guest favorite

Home in West Caldwell

4.96 out of 5 average rating, 146 reviews

Designer Cottage -historic estate -oasis

Relax in a cozy cottage (to yourself) set on a private historic estate outside of NYC (apx 20 miles)-walking distance to shops, restaurants, plus. "Oasis in a metropolis". Designed to inspire. This one of a kind space offers you studio area, bed area, eat in kitchenette, full bath and deck to enjoy gardens. Great for business travel or getaway. You'll love the vintage characteristics of the cottage, combined with lots of charm. Skip the hotel and relax. An experience to remember.

Guest favorite

Home in Greenwood Lake

4.99 out of 5 average rating, 160 reviews

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Guest favorite

Home in Boonton

4.94 out of 5 average rating, 119 reviews

Boonton Revival- A restored treasure in NJ

The Boonton Revival is an updated 100-year-old home within walking distance of historic Main Street, quaint restaurants, and unique shops. The nearby train and bus stations can connect to the NYC Port Authority (7th Ave) in one hour. Newark Liberty Airport is a 30-minute ride, and you can be at the Jersey Shore in an hour! The property owner is an avid gardener and guests are welcome to admire the koi pond and sample in-season vegetables.