Holiday rentals in Greenwich

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Top-rated holiday rentals in Greenwich

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

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Top guest favourite
A well-lit bedroom is showcased, featuring a spacious bed with plush pillows. Tasteful art pieces are displayed on the wall, and a mirror stands beside the bed. A built-in shelving unit provides storage, while a door leads to the adjacent lounge area.
Guest suite in Cos Cob
4.94 out of 5 average rating, 69 reviews

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!

Guest favourite
A modern kitchen features white cabinetry and sleek stainless steel appliances. The spacious layout includes a large refrigerator, a built-in oven, and a dishwasher. Natural light enters through nearby windows, illuminating the stylish countertops and a decorative rug that adds warmth to the space.
Flat in Stamford
4.94 out of 5 average rating, 127 reviews

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

Superhost
Flat in Greenwich
4.74 out of 5 average rating, 396 reviews

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.

Top guest favourite
The entrance to the building is framed by lush greenery on either side. A set of steps leads to a gray door adorned with decorative molding and a prominent house number. An American flag is displayed above, indicating a welcoming entry.
Flat in Greenwich
4.96 out of 5 average rating, 81 reviews

Twenty-One ! Boutique Stay (2C) Greenwich, CT

Twenty One, the charming historic pre-war building. Located in the heart of downtown Greenwich, CT. Tucked away quietly off lower Greenwich Avenue. This newly furnished, second floor unit offers charm, convenience and privacy. With a plethora of the most coveted restaurants and shops that Greenwich has to offer. Grigg St is within a block walking distance to the train station.. A car is not even needed for your next visit! NO ON SITE PARKING. Large lot across the street $5/day

Top guest favourite
Flat in Greenwich
4.95 out of 5 average rating, 105 reviews

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.

Top guest favourite
A welcoming entryway is highlighted by a wooden bench and wall hooks, ideal for hanging coats. The view leads into a modern kitchen, featuring sleek cabinetry and an open layout. Soft lighting and warm wood floors create an inviting atmosphere.
Home in Byram
4.93 out of 5 average rating, 29 reviews

1Bd Apartment 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.

Guest favourite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guest house in Pound Ridge
4.94 out of 5 average rating, 114 reviews

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.

Top guest favourite
A spacious lower level studio features a cozy seating area with a reclining sofa and a wooden coffee table. A small kitchenette with a mini-fridge and sink is visible. A large smart TV is mounted on the wall, and natural light enters from a nearby door.
Guest suite in Cos Cob
5 out of 5 average rating, 43 reviews

Cozy Cos Cob Studio

This cozy and charming space is perfect for business professionals and/or travelers looking to explore the beautiful surroundings of Greenwich. The suite is within walking distance to Pomerance Park, a scenic 107 acre hiking trail, and a variety of restaurants, making it the ideal location for outdoor enthusiasts and foodies alike. Galley kitchen, Queen bed, Full bathroom with luxury products, Workspace, Washer and Dryer, Reclining sofa, Workout room

Guest favourite
A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.
Guest house in Greenwich
4.95 out of 5 average rating, 108 reviews

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.

Top guest favourite
Home in West Side
4.99 out of 5 average rating, 188 reviews

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.

Guest favourite
Home in Harbor Point
4.8 out of 5 average rating, 152 reviews

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.

Top guest favourite
A bright living area features a large window providing natural light. A comfortable couch and a loveseat are arranged around a wooden coffee table. A decorative mirror hangs on the wall, and a flat-screen TV is positioned on a stand beside a small side table.
Flat in Stamford
4.97 out of 5 average rating, 225 reviews

Standalone Cottage surrounded by woods

Cottage on property in North Stamford. 20 minutes from Stamford Town Centre. Less than hour train to New York City. Sleeps 4 comfortably (pullout couch in living room, plus main room). Away from main house and surrounded by wooded area.

Popular amenities for Greenwich holiday rentals

When is the best time to visit Greenwich?

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Avg. price€ 149€ 133€ 145€ 156€ 175€ 190€ 186€ 181€ 176€ 181€ 180€ 188
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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 € 33 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    280 of Greenwich holiday rentals include wifi 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!