
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!

Cozy Guest Suite in Greenwich, 1mi from train
A light-filled studio with private entrance in a newly renovated home. Nestled on a very quiet street, it offers a queen size bed with private bathroom and lounge space (sofa bed) . The space small kitchen amenities include a refrigerator, coffee machine, kettle and microwave, Wi-Fi and private bathroom with shower are additional features. Other things to note As we are a young family looking for total quiet during your stay? We may not be the best hosts for you. Otherwise, please reach out!

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

Flex Comfort Apts of Greenwich #1
Flex Comfort Apt #1 is 1 BR / 1 BA and sleeps 4. Apt #1 is the bottom floor ('Basement') of a 3 apt building. Private Parking & Entrance. Great mattresses, linens, big screen smart TVs, multiple desks, and clean. Well stocked kitchen to put on a family meal. Get the value of 2 x hotel rooms for the price of one that includes your own kitchen and Family Room. 1 Mile from Greenwich Train station - 45 mins to Grand Central. Easy access to 95 and everything CT & NY have to offer.

Walk to Greenwich Ave [KING bed] BEST Location
Sun drenched unit in the heart ♥️of Greenwich by a Superhost :) Enjoy a quick walk to the bustling Greenwich Ave and all it offers, train station, Whole Foods, wonderful restaurants and night life. This spacious duplex unit with private entrance, private outdoor area & excellent soundproofing gives you the feel, QUIET and privacy of an in-town single family home. This perfect location is a nice getaway or a WFH stay with KING bed, Full kitchen, updated appliances, Speedy WiFi⚡️& SMART TVs

1Bd Cottage in Greenwich | Designer Stay near NY
Modern Designer One-Bedroom Retreat | Near NY & CT. Experience luxury and comfort in this stylish one-bedroom apartment designed by a professional interior designer @dacasabypriscilla. Featuring high-end finishes, curated décor, and abundant natural light, this serene hideaway blends modern design with convenience. Nestled in a peaceful setting yet minutes from major highways, it offers easy access to Connecticut and New York—perfect for business travelers or weekend getaways.

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.

Gem by the water+ firepit and all fenced backyard
Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

French Guest House in Waccabuc
A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

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.)
Popular amenities for Greenwich holiday rentals
Stay near Greenwich's top sights
Other great holiday rentals in Greenwich

Sun Room

2 Greenwich walk to train 10 mins

Private Room Twin XL Bed in Greenwich, CT

Private basement bedroom /bathroom in family home

_Simon’s Sage Room

Sunshine Room by harbor downtown beach, I-95&Train

Comfy Room w. Queen Bed | near Downtown & Train

Stylish Greenwich Guesthouse
When is the best time to visit Greenwich?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $253 AUD | $225 AUD | $246 AUD | $264 AUD | $297 AUD | $321 AUD | $315 AUD | $307 AUD | $298 AUD | $311 AUD | $311 AUD | $312 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 180 vacation rentals in Riverside, over 70 vacation rentals in Purchase, and over 180 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 bed and breakfast rentals in Greenwich have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Greenwich. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in condo rentals in Greenwich?
Experience the best of Greenwich with our condo rentals, starting at about $70 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 house rentals in Greenwich have wifi?
Absolutely! We offer over 130 house 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 280 holiday rentals in Greenwich

Nightly prices starting at
Greenwich holiday rentals start at $57 AUD per night before taxes and fees

Verified guest reviews
Over 11,240 verified reviews to help you choose

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

Pet-friendly accommodation
Find 110 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
280 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
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- Brooklyn Bridge
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- Ohel Chabad-Lubavitch
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- Statue of Liberty




