
Holiday houses in Greenwich
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Top-rated holiday rentals in Greenwich
Guests agree: these stays are highly rated for location, cleanliness and more.

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!

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

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.

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.

Cozy&Chic 1Bd 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.

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.

Bright 2BR Greenwich Suite•Spa Tub & Massage Chair
A refined top-floor 2BR sanctuary with private entrance and parking, created for guests seeking elevated comfort and tranquility. Renovated with hardwood floors, a fully equipped kitchen with reverse-osmosis water, and a spa-style bathroom with a jetted soaking tub, bidet, and filtered shower. Unwind in the full-body massage chair and enjoy the naturally calming, healing energy praised by many guests. Ideal for restorative, wellness-focused stays.

Stamford’s Island Inspired Efficiency
This island-themed efficiency apartment offers comfort, style and convenience. After waking up on the memory foam mattress and before enjoying all the conveniences that downtown Stamford has to offer, or taking the nearby train to Manhattan, start your day by waking up to turquoise waters and seashells, sipping on different flavors of coffee or tea, and snacking on the light breakfast items provided.

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.

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

Our COZY and convenient home

Sun Room

Small cozy room in historic 1828 Dobbs Ferry home.

Private Room Twin XL Bed in Greenwich, CT

Country Cottage

Spacious Clean & Cozy Private Room + Bath

Quiet room in the heart of Westchester

Cos Cob, Greenwich garden studio
When is the best time to visit Greenwich?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $267 AUD | $237 AUD | $260 AUD | $279 AUD | $313 AUD | $339 AUD | $333 AUD | $324 AUD | $315 AUD | $324 AUD | $321 AUD | $336 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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- Rentals with a washing machine and dryer Greenwich
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- Pet-friendly rentals Greenwich
- Family-friendly rentals Greenwich
- Rentals with beach access Greenwich
- Rentals with a fire pit Greenwich
- Condo rentals Greenwich
- Rentals with a fireplace Greenwich
- Rentals with outdoor seating Greenwich
- Rentals with pools Greenwich
- House rentals Greenwich
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- Fitness-friendly rentals Greenwich
- Rentals with breakfast Greenwich
- Rentals with a hot tub Greenwich
- 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




