Vacation rentals in Paradise Island

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Top-rated vacation rentals in Paradise Island

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

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Guest favorite

Home in Woodstock

4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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Home in Ossining

4.84 out of 5 average rating, 146 reviews

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Top guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 197 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

Guest favorite

Apartment in Ossining

4.94 out of 5 average rating, 136 reviews

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

Unwind at this peaceful retreat a short walk from downtown Ossining and Hudson River front parks. Designed with end to end comfort, beautifully decorated, and featuring a gorgeous open kitchen and entertaining room, in this space you can relax and step away from it all. Highlights include: 2nd floor walk-up High End Appliances and all Finishes Heated bathroom floors Contactless entry Off-street parking 1/2 block from multiple parks Weekly discount available Come stay here! You’ll love it

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Apartment in Peekskill

4.8 out of 5 average rating, 170 reviews

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Top guest favorite

Guesthouse in Mahopac

4.95 out of 5 average rating, 235 reviews

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

Top guest favorite

Guest suite in Croton-on-Hudson

4.92 out of 5 average rating, 135 reviews

The Bluestone - Spacious 2 bedroom w/central air

Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: Drive, walkway and entrance accessible to full size wheelchair (see photos) however the bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

Top guest favorite

Cottage in Weston

4.97 out of 5 average rating, 143 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Top guest favorite

Tent in Livingston Manor

4.98 out of 5 average rating, 142 reviews

Milkweed Camp - Glamping in a Blueberry Field

Our off-grid canvas tent is situated at the edge of a meadow, surrounded by blueberry bushes. It's just 4.5 miles to Main St in Livingston Manor, and 35 minutes to Bethel Woods. We provide a full-size bed (w/ heated mattress pad), fire pit, firewood, propane heater, and solar power. You have access to a private outhouse with composting toilet & outdoor shower on-site, and a conventional shared bathroom if you preferred. We are an LGBTQ+ inclusive space.

Guest favorite

Cottage in Pawling

4.98 out of 5 average rating, 124 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Guest favorite

Guest suite in Haverstraw

4.94 out of 5 average rating, 365 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:)

Top guest favorite

Barn in Mount Kisco

4.91 out of 5 average rating, 579 reviews

NY Rustic Cottage Getaway

Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

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Popular amenities for Paradise Island vacation rentals

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Other great vacation rentals in Paradise Island

Guest favorite

Cabin in Wurtsboro

4.97 out of 5 average rating, 332 reviews

Spring Spa on a Cascading Brook - The Water House

AndreaRating, 5 stars2 weeks ago

This was our 3rd or 4th time here. Obviously we love the place! We have noticed improvements over the year, James and Irene take good care of this property. Had a small hiccup this visit and James was understanding and kind. This place is magical and its owners are responsive and helpful.

Guest favorite

Private room in Peekskill

4.88 out of 5 average rating, 102 reviews

Spacious Room in Colonial Home Close to NYC

HaroonRating, 5 stars1 week ago

Great host

Guest favorite

Apartment in Ossining

4.88 out of 5 average rating, 16 reviews

The Yellow Brick Getaway

NadiaRating, 5 stars2 weeks ago

Enjoyed our stay and found Melita very helpful, friendly and proactive with advice. We had hired a car and needed parking permit and she took care of getting the required permit as well as taking care of the parking fine we received due to our misunderstanding of the conditions. Thank you Melita.

Guest favorite

Guest suite in Chester

4.96 out of 5 average rating, 319 reviews

Adorable Guest Apartment in Victorian Mansion

RyanRating, 5 stars3 weeks ago

Chad and Anastasia place is like how they say it is. It is built with love and care, it really showes in how they renovated the place and how they decorated the place. I appreciated their friendliness and their kindness in communicating with us, we had some minor problem with the unit but they responded quickly and handled it professionally. I highly recommend booking with them good people with good values, I would definitely come back to Chad and Anastasia's place.

Home in Philipstown

5 out of 5 average rating, 9 reviews

Arkadia House Mid-century retreat with pool & view

AriRating, 5 stars71 months ago

Dan and Andrew were great hosts and very easy to communicate with. The location was beautiful and the views were amazing. The house was stocked with everything you could possibly need; towels, bedsheets, blankets cookware, a bunch of basic food necessities & more. The pool was refreshing after laying in the sun and watching the sunset from the pool is truly a must when visiting this home. We would love to stay here again and highly recommend to others looking for a gorgeous getaway home.

Top guest favorite

Apartment in Ossining

4.96 out of 5 average rating, 441 reviews

Hudson River Peaceful Getaway, Explore from here

NicoleRating, 5 stars6 days ago

What a beautiful place to stay in the Hudson Valley. The view from the property is just breathtaking. Dan’s place is very clean, open and beautifully furnished. We can’t wait to come back!

Superhost

Apartment in Newburgh

4.86 out of 5 average rating, 190 reviews

Special Nest w Private Entrance River View Porches

AnalieseRating, 5 stars2 weeks ago

Our stay here in Newburgh was lovely! This place was well-stocked, very very clean, fabulously eclectic, and spectacularly spacious! We loved having two restrooms and being so close to the river and to Hudson Taco!! As the Host mentions, do carefully consider how much you care about “neighbor noise.” While I brought slippers to kindly observe the “no shoes in the house” rule, the tenants above us rudely did not. We couldn’t hear voices, but the heavy footsteps kept us awake until 1 o’clock in the morning on a weeknight and woke us up at 6:30 AM on Saturday morning. The dog scampering around or crying and whining loudly every time it was left alone in the house was also hard to bear despite our bringing ear plugs. We would 100% stay again if Sarah would kindly have us. We’re sure to have more considerate neighbors next time. Thank you for creating such a lovely space at an affordable rate.

Top guest favorite