
Holiday houses in Greenwich
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Top-rated holiday rentals in Greenwich
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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!

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!

Luxurious 1BR Downtown Stamford
Step into your luxurious haven in the heart of downtown Stamford, where opulence seamlessly meets comfort and indulgence becomes your personal mantra. From the impeccable design and luxurious amenities to the prime location, every moment spent here is a celebration of the finer things in life. Treat yourself to an extraordinary stay, crafting memories that will linger in your heart for a lifetime . Welcome to a world where luxury knows no bounds, and warm hospitality eagerly awaits your arrival

Overlook Cabin in downtown Greenwich CT
Last house on a private road, parking onsite if 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.

The Cozy Little Cottage
Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

Special Nest w Private Entrance River View Porches
Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Cozy 2 BR Greenwich Apt. with easy access to NYC
Cozy two bedroom apartment on a quiet street in Greenwich with brand new appliances. Walking distance to Metro North train station, beach, park, tennis court, pickle ball court, restaurants, shops. Just 38 minutes from NYC. Few minutes drive to downtown. Fully stocked kitchen and laundry with everything you may need. Living room with 65" Smart TV. Master BR with 45" Smart TV. The apartment is professionally cleaned & sanitized up to CDC guidelines & inspected before each stay.

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

The Cottage in Greenwich
Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING
Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Charming private 1BR apt. Easy access to NYC
Location, location, location! Private 1 bedroom unit that is part of a two-unit property. It has its own entrance, kitchen, bath, and off street parking. Walkable to Valhalla Metro North train station. (Has steps and stairs. No children under 12 years old.)

Small Studio. Private Entrance and bathroom
Welcome, this is a small and cozy studio for one person located in a quiet and safe area near Harbor Point with a private entrance, private bathroom, and a small kitchenette. 1 miles from downtown and a 3 minutes drive to the train station and I95.
Popular amenities for Greenwich holiday rentals
Stay near Greenwich's top sights
Other great holiday rentals in Greenwich

Cozy&Chic 1Bd in Greenwich | Designer Stay near NY

Stamford Grand Apartment + Cozy Den

Downtown gem w/ parking, Wi-Fi+!

Riverfront Cottage-Pool-Hot Tub-Fireplace 35m>NYC

Luxury designer home with garage in Greenwich

Beautiful Cottage in Greenwich CT

Walk to Greenwich Ave [KING bed] BEST Location

Solara – Luxury 1BR Downtown
When is the best time to visit Greenwich?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $269 AUD | $239 AUD | $261 AUD | $281 AUD | $315 AUD | $341 AUD | $335 AUD | $326 AUD | $317 AUD | $326 AUD | $323 AUD | $338 AUD |
| Avg. temp | 1°C | 2°C | 6°C | 12°C | 18°C | 23°C | 26°C | 25°C | 22°C | 15°C | 10°C | 4°C |
Frequently Asked Questions
Where should I stay in Greenwich?
Make yourself at home in Greenwich by choosing from our most frequently booked neighborhoods. We have over 170 vacation rentals in Riverside, over 70 vacation rentals in Purchase, and over 170 vacation rentals in Cos Cob.
Are there vacation rentals with a dedicated workspace in Greenwich?
Yes! Work meets play with ease at over 170 vacation rentals in Greenwich featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Greenwich?
Four-legged friends are welcome in Greenwich. Choose from more than 100 vacation rentals for guests traveling with pets.
Are there Greenwich vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Greenwich, available on Airbnb. Make a splash and soak up the sun in style!
Do private suite rentals in Greenwich have air conditioning?
Absolutely! We offer over 10 private suite rentals with air conditioning in Greenwich. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Greenwich?
Experience the best of Greenwich with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Greenwich have a gym?
Absolutely! We offer over 40 house rentals with a gym in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Greenwich have wifi?
Absolutely! We offer over 60 apartment rentals with wifi in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenwich have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Greenwich?
Greenwich has more than 20 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Greenwich

Total holiday rentals
Explore 260 holiday rentals in Greenwich

Nightly prices starting at
Greenwich holiday rentals start at $60 AUD per night before taxes and fees

Verified guest reviews
Over 10,460 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 100 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
260 of Greenwich holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Greenwich rentals

4.8 Average rating
Greenwich stays are highly rated by guests—averaging 4.8 out of 5!
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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- New York Public Library - Bloomingdale Library
- Grand Central Terminal
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Yale University
- Mountain Creek Resort
- Jones Beach
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Fairfield Beach
- Empire State Building
- Radio City Music Hall
- Statue of Liberty
- Canarsie Beach
- Rye Beach
- USTA Billie Jean King National Tennis Center
- McCarren Park
- The Metropolitan Museum of Art




