Cottage vacation rentals in Bear Mountain

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Top-rated cottage rentals in Bear Mountain

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Guest favorite

Cottage in Cortlandt

5.0 out of 5 average rating, 105 reviews

Cottage at Peekskill Hollow

Romantic Hudson Valley cottage just 1 hour outside NYC in northern Westchester! Beautiful, wooded location along the Peekskill Hollow Creek - just off the beaten path. You’ll be surrounded by nature and still be a hop, skip and jump away from restaurants, shopping, hiking/bike trails, West Point, the Hollow Brook Golf Club and historic sites (Revolutionary War, Rockefeller, Roosevelt, Underground Railroad). Quick access (by car or train) to/from NYC and greater Hudson Valley. High speed WiFi.

May 27 – Jun 3

G$51,172 GYD per night

Guest favorite

Cottage in Greenwood Lake

4.92 out of 5 average rating, 141 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

Sep 19 – 26

G$29,129 GYD per night

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 160 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Sep 25 – Oct 2

G$27,896 GYD per night

Guest favorite

Cottage in Highland

4.91 out of 5 average rating, 538 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Sep 15 – 22

G$32,585 GYD per night

Guest favorite

Cottage in Accord

4.88 out of 5 average rating, 216 reviews

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

May 9 – 16

G$17,072 GYD per night

Superhost

Cottage in Putnam Valley

4.9 out of 5 average rating, 215 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Dec 27 – Jan 3

G$78,315 GYD per night

Guest favorite

Cottage in Monroe

5.0 out of 5 average rating, 129 reviews

Cozy Lake Cabin

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has abundant retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes Free Firewood, NO CLEANING/PET FEES🐕

Oct 10 – 17

G$75,095 GYD per night

Guest favorite

Cottage in Goshen

4.94 out of 5 average rating, 195 reviews

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Mar 11 – 18

G$27,259 GYD per night

Guest favorite

Cottage in Greenwood Lake

4.97 out of 5 average rating, 281 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

Feb 26 – Mar 5

G$70,277 GYD per night

Guest favorite

Cottage in Kerhonkson

4.94 out of 5 average rating, 257 reviews

Blue Haven in the Catskills

We built a studio-house on the foundation of an old summer cottage. We did not expand the footprint, but furnished it with select pieces and appliances and gave it contemporary finishes. We also added a screened porch, open deck and stone patio. The woodland and mountain views are lovely, while the location is convenient to Lake Minnewaska State Park and the Mohonk Preserve. Ulster County levies a 2% tax on overnight stays. Payment is made anytime between confirmation and arrival.

Sep 8 – 15

G$22,114 GYD per night

Guest favorite

Cottage in Newburgh

4.87 out of 5 average rating, 188 reviews

Cozy Lake Cottage

Cozy cottage in residential lake community, adjacent to historic fine dining restaurant. There is an approximate 150 yard walk down to the lake to enjoy the spectacular sunsets . Centrally located in the Hudson Valley near everything there is to experience. Located in our area Many Local Wineries ( Angry Orchard) Woodbury Commons Outlet Mall Historic Newburgh and Waterfront Culinary Institute of America US Military Academy New Paltz and Mohonk Mountain House

Jul 8 – 15

G$26,911 GYD per night

Superhost

Cottage in Mohegan Lake

4.92 out of 5 average rating, 170 reviews

The Pearl of Westchester

Welcome to the Paradise! This Pearl of Westchester are nested with a Main house on private 2 acres of direct waterfront estate. Offering a private dock and beach in a flawless natural paradise. Enjoy swimming, fishing, boating or barbecuing on a private porch. Hiking in walking distance Located less than an hour away from NYC. Peekskill Metro North is 15 min away.

May 28 – Jun 4

G$36,490 GYD per night