Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A red cabin with stone accents is surrounded by greenery, featuring a wooden porch with large windows. A gravel path leads to a patio area with a red umbrella, seating, and a grill in the fenced backyard, providing a welcoming outdoor space.

Cabin in Milford

4.91 out of 5 average rating, 179 reviews

Riverfront Cabin on the Delaware

Unwind on the banks of the Delaware river. Our cozy cabin has all the modern accommodations you'd expect in a vacation home paired with the outdoor amenities that make this vacation home a peaceful dream come true! Interior amenities include: WiFi, TV with cable, Nespresso Coffee Maker and Pods, Washer/Dryer, Gas Fireplace, Full Set of Pots & Pans, Pull-Out Sofa, Towels & Linens included in stay. Outdoor amenities include: Grill, Wood-Burning Firepit, Hot Tub, Corn Hole, Private River Access.

Top guest favourite

A charming house is nestled under a large, vibrant tree with red foliage. The exterior features white siding and a front porch with several seating options. A well-maintained lawn surrounds the home, providing a serene outdoor space.

Flat in Greenwood Lake

4.95 out of 5 average rating, 105 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

Top guest favourite

A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.

Cottage in Warwick

4.99 out of 5 average rating, 113 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Guest favourite

A comfortable seating area features a dark sectional sofa adorned with decorative cushions. A light-colored coffee table sits in the center, with a bowl placed on top. Natural light enters through a nearby window, while a fan overhead provides airflow.

Flat in Wallington

4.93 out of 5 average rating, 100 reviews

Cozy 10 mn to MetLife/American Dream/New York City

Nestled in a quiet and safe neighborhood located a quick 10 min from MetLife stadium, this cozy 5 star rated 1-bedroom, 1-bath retreat is perfect for up to 4 guests. Located on the 3rd floor of a quiet residence, we are happy to provide you with the ultimate in comfort and convenience during your stay. Whether you’d like to visit the American Dream mall, enjoy the sights of NYC, work remotely or visit family locally, this apartment will become your home away from home as others have discovered!

Superhost

An open living area features a stone fireplace surrounded by natural light from large windows. A comfortable seating arrangement includes a light-colored couch and a wooden coffee table on a decorative rug. High vaulted ceilings enhance the spaciousness, with the kitchen visible in the background.

Home in Greenwood Lake

4.82 out of 5 average rating, 186 reviews

Aster Place

A beautiful and cozy home nestled in the Forest Hills section of Greenwood Lake, just over an hour outside of New York City. Boasting nearby activities in each season, including wineries, skiing and lake activities, this is a perfect year-round retreat. located 1/2 mile from our quiet community beach allows for a serene daily chill by the water. Town center is a short drive away, or 15 minutes from all that Warwick has to offer, you will enjoy this perfect setting for your lakeside getaway!

Guest favourite

The living area features a modern design with light-colored walls and a cozy sectional sofa. A stone fireplace is surrounded by stylish furnishings, including a wooden coffee table. Natural light enters through large windows, creating a warm and inviting atmosphere.

Home in Greenwood Lake

4.96 out of 5 average rating, 203 reviews

Tranquil Lake Escape! Amazing views, Fireplace!

Winter is the most quiet & peaceful time to visit! Enjoy the beautiful snowy views of the frozen lake & mountains across the way at this 3BR home in Greenwood Lake!! You'll love the cozy interior & the warm wood burning stove! This tranquil hideaway on a quiet dead-end street is minutes from several winter activities. Book your retreat now! Nearby downtown Warwick, mount peter, winter hiking on the Appalachian, wineries, breweries, Mountain Creek resort and Spa, and more! ~ 1 hour from NYC

Top guest favourite

A modern full kitchen is equipped with stainless steel appliances, including a gas stove and fridge. A butcherblock table is positioned under natural light, with seating for two. The overall color scheme features gray cabinets and light wood flooring, enhancing functionality and style.

Home in Piermont

4.97 out of 5 average rating, 116 reviews

Piermont's Getaway Mt. Village Home. 30min to NYC

Nestled at the base of Tallman Mountain lies the quaint village of Piermont where a population of 2,500 sleep, live, thrive and enjoy life on the simpler side. Sip a coffee on the porch overlooking the Sparkill creek, take a stroll down Main Street for an array of options to visit. Fishing on the pier, dancing fireflies at night and wildlife throughout. A quick hike up the backyard mountain to the state park where you can enjoy a picnic and view of the Hudson while catching a glimpse of NYC.

Guest favourite

A spacious outdoor deck overlooking the lake is furnished with comfortable seating, including a sectional sofa and lounge chairs. Two large umbrellas provide shade, and a potted plant adds a touch of greenery, enhancing the tranquil lakeside setting.

Home in Andover

4.94 out of 5 average rating, 320 reviews

Stay at beautiful Leisure Lake Lodge

Leisure Lake Lodge is located on beautiful Lake Hopatcong just 1 hour from NYC. You'll fall in love w/ stunning lake views from all 3 levels of this large home, two massive decks over the lake & totally updated home easily sleeps 9. Fireplace, hot tub, sauna, foosball, ping pong, grill, 65" UHD TV, fully equipped newer kitchen, newer bathrooms, newer mattresses, 50 ft lake frontage w/ 80 ft dock, 32x20 ft boathouse w/ 400 SF deck over the lake & 19x12 ft 4-season game room with ping pong.

Top guest favourite

A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.

Cabin in Greenwood Lake

4.96 out of 5 average rating, 466 reviews

Cabinessence -on Greenwood Lake, NY #34370

"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!)

Guest favourite

A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.

Home in Putnam Valley

4.98 out of 5 average rating, 105 reviews

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Top guest favourite

A quiet front porch features a comfortable seating area with plush cushions. Hanging plants and string lights add a touch of charm. The view includes a tree-lined street, with parked cars visible in the soft glow of evening light.

Flat in Montclair

4.97 out of 5 average rating, 109 reviews

Updated private two bedroom in heart of Montclair

A complimentary bottle of red wine is included with each stay by default. The space is quiet for Montclair yet centrally located. Our cleaner Mikki is responsible for cleaning and preparing the space. She takes great pride in her work, and we’re lucky to have her. The entire cleaning fee goes to her. I travel almost exclusively using AirBnb. If you value a space to be exclusively yours, as I do, this is likely the AirBnb for you. It would be a privilege to host you 🙂. Cheers, Alex

Guest favourite

An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.

Cottage in Greenwood Lake

4.98 out of 5 average rating, 376 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 #33593