Holiday rentals with outdoor seating in Westchester County

4.9 out of 5 average rating, 112 reviews

Home in Rye

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

4.96 out of 5 average rating, 204 reviews

Sugar Shack Studio | Downtown Skyline Views

Location! Studio apartment located in the heart of downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and a short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 10 minute walk. Washer and Dryer included in the building with credit card payment. This unique place has a style all its own!

4.8 out of 5 average rating, 170 reviews

Apartment in Peekskill

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.

4.91 out of 5 average rating, 154 reviews

Home in Yorktown Heights

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms and a POOL. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & pack n play. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

4.89 out of 5 average rating, 119 reviews

Cabin in Greenwich

Overlook Cabin in downtown Greenwich CT

Last house on a private road, two parking spaces available, conveniently located walk to train station, Greenwich Avenue in Greenwich CT to the ferry, Sherman Park for beach access. Travel to New York City in 37 minutes with the Metro-North Express train. We are at one of the highest points on the Greenwich Coastline. You can hear the sounds of life: from church bells ringing, the train to NYC and Rt 95 traffic, NO SMOKING NO parties NO events Sorry NO PETS service animals always welcomed.

5 out of 5 average rating, 107 reviews

Cottage in South Salem

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

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.

4.97 out of 5 average rating, 124 reviews

Barn in Katonah

The Magic Red Barn with heated pool now opened!

Experience country magic one hour from NYC! Our heated saltwater pool offers a perfect retreat. Enjoy nearby farmers' markets, Muscoot Farm, and scenic orchards. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn that includes: 1 king , 2 queen , and 1 toddler beds, a full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests who need to « escape ». Enjoy privacy—no other guests. Good Wi-Fi and full-house generator.

4.96 out of 5 average rating, 441 reviews

Apartment in Ossining

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

4.9 out of 5 average rating, 140 reviews

Apartment in Yonkers

Elegant Riverfront Getaway with Beautiful Views

Escape to this elegant historic home with stunning Hudson River views. This tastefully decorated one-bedroom apartment boasts a beautiful balcony overlooking the water and a luxurious resort-style spa with a palatial steam room and jetted tub. The home offers a warm and relaxing ambiance, perfect for a romantic getaway, a peaceful family vacation, or a tranquil weekend. Located just a few blocks from the Greystone Metro North, you can reach NYC in under 45 minutes.

4.96 out of 5 average rating, 123 reviews

Apartment in Yonkers

Private Apartment in Park Hill Yonkers

Private700+ square foot apartment in the peaceful, historic Park Hill neighborhood of Yonkers, yet still close enough to enjoy all the excitement of New York City. This large, sun-drenched apartment is situated in a beautiful 1920's English Tudor home and has its own private entrance. It offers one and a half baths. The queen bed has a comfortable 12" memory foam mattress and the spacious living room has a large sectional, board games and a 55" LG smart TV.

Guesthouse in Hastings-on-Hudson

4.92 out of 5 average rating, 848 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, private Shangri-La with backyard chickens in the artistic and quaint Rivertowns, 35 minutes from NYC along the Hudson River. The Tiny House escape is reminiscent of sleepaway camp (rustic), yet tastefully curated with eclectic art and furnishings. Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking. Read on…

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Popular amenities for Westchester County outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.87 out of 5 average rating, 78 reviews

Home in Chappaqua

Chic and Cozy 2BD 1920's Cottage Retreat

VanessaRating, 5 stars4 weeks ago

Elizabeth’s place was great and we thoroughly enjoyed our stay! It had everything we needed to be comfy with our toddler and dog, and the neighborhood had all we needed as well (close to the train station, great coffee at Bobo’s and Lange’s deli for breakfast and lunch). Elizabeth made sure we got in okay and was very responsive. Thanks!

Home in Hastings-on-Hudson

4.78 out of 5 average rating, 63 reviews

Rivertown Retreat 25 mins to NYC

BethRating, 5 stars2 weeks ago

This place is very spacious and well located for a short walk to stroll along the Hudson River, shops & restaurants. Having a driveway to use for parking is a huge draw. Kitchen is well stocked to prepare whatever you'd like to prepare. We would definitely stay here again when in the area. Host was very responsive if we had any questions.

4.93 out of 5 average rating, 84 reviews

Home in Bedford

Bedford Paradise Getaway | Hot Tub | Town Center

LaurenRating, 5 stars2 weeks ago

Cozy home, well located to pop into Bedford Village for morning coffee and a casual dinner. Perfect launchpad to spend a weekend exploring. Styled by an interior designer.

5 out of 5 average rating, 37 reviews

Home in Pound Ridge

Historic wooded 3BD 1 hour from NYC

SabrinaRating, 5 stars1 month ago

We had the most magical stay at Keely’s place. Her home is beautiful and smelled amazing. Thriving plants, surfaces of wood and stone - a true naturalist’s refuge. The picture windows overlooked gardens bursting with flowers. We meandered from the backyard onto hiking trails through the woods, lounged on the deck in the sun and savored the tranquility. Perhaps the best Airbnb we’ve ever encountered. 10/10

4.96 out of 5 average rating, 45 reviews

Home in Greenwich

Riverfront Cottage Retreat & Pool 35 mins from NYC

Rich Rating, 5 stars1 week ago

A truly Great stay in Greenwich with David, we really enjoyed our stay in the house, such an awesome place and quiet location (next to a beautiful river!) too, which we loved. The pool was a massive bonus for sure! Comms with David were great, he was very quick to respond at all times on any queries we had, much appreciated indeed. Many thanks again, Rich

5 out of 5 average rating, 164 reviews

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MeredithRating, 5 stars3 days ago

Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!

4.84 out of 5 average rating, 160 reviews

Home in Stamford

Gem by the water+ firepit and all fenced backyard

KellyRating, 5 stars3 days ago

This was a charming, clean and convenient place to stay. Maritza's little touches and great communication made it easy and enjoyable.

4.95 out of 5 average rating, 185 reviews

Home in Nyack

Chic Vintage Cottage in Artsy Village of Nyack

ColleenRating, 5 stars3 weeks ago

Chandra’s place was perfect for our stay. It’s incredibly quiet although close to a highway. It had everything we could need, even coffee available for use which was great. Beautiful home! Thank you Chondra!

Show all

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 64 reviews

Apartment in Tarrytown

2 BRs, Easy Walking in Tarrytown and Sleepy Hollow

ElleRating, 5 stars1 day ago

This was such a fantastic place to stay as a family. Drew is very kind and welcoming. The place is decorated so beautifully and is comfortable, clean, and relaxing! thank you very much!

4.86 out of 5 average rating, 192 reviews

HighLineHarbor Flat2BD|Train2NYC|HarborPointAccess

RachelleRating, 5 stars1 month ago

Martin was a fantastic host and communicator. His place was perfect and we had a wonderful time. Would stay here again!

4.98 out of 5 average rating, 99 reviews

Luxurious 1BR Downtown Stamford

SarahRating, 5 stars3 weeks ago

The overall cost was a bit pricey, but the responsiveness of Lavish & Live and being downtown and included parking made the price more reasonable. I would book again.

4.83 out of 5 average rating, 128 reviews

Apartment in Nyack

Nyack Retreat

TaraRating, 5 stars4 months ago

Nice and easy place to stay close to town can walk….host was responsive to my questions…will rent again from here

Apartment in Mohegan Lake

4.81 out of 5 average rating, 176 reviews

Yellow House one bedroom

AliciaRating, 5 stars1 month ago

Great cozy spot to visit family, with easy access to restaurants, shopping, and the highway. The apartment has a private entrance from the main house and has everything one would need for a stay.

5 out of 5 average rating, 13 reviews

Apartment in Greenwich

Greenwich Garden Apartment

ElizabethRating, 5 starstoday

We were a party of three in town visiting friends that live five minutes away. Immediately upon walking in, you can feel how clean and well maintained the space is. What a great townhouse with private parking and so much space inside the home. Even though we were only there one night, the home was equipped with everything you would need if you wanted to cook a full meal. Thank you for your hospitality!

4.93 out of 5 average rating, 220 reviews

Apartment in Mamaroneck

2 Bed/1 Bath Private Apartment in Mamaroneck

MarkRating, 5 stars3 weeks ago

The apartment was very clean, in a great location near lots of shops and restaurants and well equipped. It’s also walking distance to the Emelin Theatre which hosts a wide variety of shows. Elizabeth was quick to respond to a few questions.