Holiday houses in Greenwich

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Greenwich

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Rye

4.9 out of 5 average rating, 112 reviews

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!

Guest favourite

Apartment in Stamford

4.82 out of 5 average rating, 181 reviews

Sunset Retreat: 1BR Walking Distance to the Beach

Welcome to our charming and spacious 1 bedroom Airbnb in the heart of the beach district in Stamford! This delightful 1st fl apartment offers everything you need for a memorable stay. Prime location offers the best of both worlds. Just a short 5-min stroll will take you to the local train station, providing easy access to neighboring cities and attractions. Additionally, downtown Stamford is a mere 7-min drive, where you can indulge in a wide array of dining, shopping, and entertainment options.

Guest favourite

Home in White Plains

4.92 out of 5 average rating, 120 reviews

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

Top Guest favourite

Home in Putnam Valley

4.99 out of 5 average rating, 108 reviews

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Guest favourite

Cabin in Greenwich

4.89 out of 5 average rating, 119 reviews

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.

Top Guest favourite

Cottage in South Salem

5 out of 5 average rating, 107 reviews

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 favourite

Cottage in Greenwood Lake

4.98 out of 5 average rating, 343 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

Top Guest favourite

Apartment in Ossining

4.96 out of 5 average rating, 441 reviews

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.

Top Guest favourite

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

Superhost

Loft in Stamford

4.94 out of 5 average rating, 207 reviews

Luxury Loft Apt. with easy access to NYC & CT

Gorgeous and modern 2 bedroom apartment in Harbor Point area. Walking distance to the train station , restaurants, parks, shops, waterfront boardwalk and just 48 minutes from the Big Apple. Few minutes drive to downtown. A large kitchen and laundry with everything you may need and a spacious living room with 48 inch TV cable access and internet.The apartment is professionally cleaned & sanitized up to CDC guidelines & inspected before each stay to ensure your safety.

Top Guest favourite

Home in Downtown Stamford

4.99 out of 5 average rating, 135 reviews

45 Minutes from NYC | Urban Hideaway in Stamford

Welcome to our charming home! Escape the city and unwind in this fully equipped house, just 5 minutes from downtown Stamford, CT. We’re conveniently located 5 minutes from I-95, as well as Cove Island and Shippan Beach, top restaurants, parks, grocery shops, and pharmacies. Our house is only 45 minutes from New York City. It’s the perfect spot for a fun and relaxing stay! With thoughtfully curated decor and all the comforts you need, you’ll truly feel right at home.

Guest favourite

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.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

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

Apartments

Convenient locations with everyday essentials

Popular amenities for Greenwich holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Greenwich

Superhost

Townhouse in Greenwich

4.95 out of 5 average rating, 74 reviews

Quaint duplex + pvt yard. Walk to town & beach!

BarbaraRating, 5 stars1 month ago

Very comfortable, lovely furniture, great beds, adjustable temperature for each area. Well stocked kitchen with everything you need. The stairs are are narrow, maybe tricky for some guests with mobility issues. The outdoor spaces are fantastic and private. Safe area with lots to do. Highly recommend for family or small groups!

Guest favourite

Apartment in Downtown Stamford

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.

Guest favourite

Apartment in Greenwich

4.96 out of 5 average rating, 56 reviews

Great hotel alternative, near Greenwich train stn

JocelynRating, 5 stars3 weeks ago

This place was beautiful and very clean. Loved the proximity to town and the porch. Great stay!

Top Guest favourite

Condo in Stamford

5 out of 5 average rating, 16 reviews

Comfortable, Beautiful Apartment-Close to Downtown

KarenRating, 5 stars2 weeks ago

I am new to the Stamford / Greenwich area and needed a place to stay while I looked for a permanent residence. I stayed at Juan's place for about 3.5 months. It was very convenient to Greenwich (where I work) and to downtown Stamford (restaurants and shops) and the Stamford train station, which has great express trains to NYC. It is also very close to a grocery store and several gyms (I chose Orange Theory, only a few blocks away). I chose Juan's place for the location and king size bed. The bed was very comfortable, the towels were great and the overall unit worked really well for myself and my husband - it has wifi and we connected to our Netflix & other apps thru the smart TV. It fits two people comfortably and has a pull out sofa for guests (my college-age children visited a few times). The kitchen has what you need, including a dishwasher. There is one permanent parking space available and several guest spots. Juan was very responsive and a great host. Highly recommend!

Superhost

Home in Stamford

4.84 out of 5 average rating, 160 reviews

Gem by the water+ firepit and all fenced backyard

KellyRating, 5 stars2 days ago

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

Guest favourite

Apartment in Downtown Stamford

4.98 out of 5 average rating, 51 reviews

Stamford Grand Apartment

KarlaRating, 5 stars1 month ago

We had a wonderful weekend in Stamford. The apartment was very nice. The location was convenient. We took the train into NYC for a Broadway show. It was very easy. We would definitely do this again.

Guest favourite

Home in Greenwich

4.91 out of 5 average rating, 56 reviews

Super SAFE 2.5 bds Greenwich Healing Sanctuary

CarolRating, 5 stars2 months ago

Enjoyed our stay and Inessa was a great host, we had some questions while we were here and she always responded very quickly. Beds in both bedrooms were very comfortable and kitchen had basic needs for a short stay. Place was very clean and it was so convenient to have the washer/dryer in the unit. Also loved the touch of having live flowers on the table when we arrived and a sweet treat that was left by the host. We would definitely stay here again location also very convenient to stores and restaurants and to our families.

Guest favourite