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.

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Guest favourite
A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.
Home in Rye
4.91 out of 5 average rating, 139 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!

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, 70 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!

Top 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.
Apartment in Stamford
4.95 out of 5 average rating, 129 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
Apartment in Greenwich
4.75 out of 5 average rating, 398 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
A spacious living area is seen, featuring a blend of comfortable seating options, including two sofas and several armchairs. A coffee table sits on a large area rug, and a dining table is positioned nearby. Natural light floods the room through multiple windows, enhancing the bright atmosphere.
Townhouse in Greenwich
4.92 out of 5 average rating, 134 reviews

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

Top Guest favourite
A modern living space features a stylish kitchen with white cabinetry and stainless steel appliances. An inviting seating area includes a light-colored sofa and a round coffee table. Natural light streams in, accentuating the neutral color palette and decorative accents, including a floral artwork.
Home in Byram
4.94 out of 5 average rating, 31 reviews

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.

Top Guest favourite
Apartment 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.

Superhost
A well-lit living room features a light-colored sofa adorned with cushions, paired with a wooden coffee table. A television is mounted on the wall, while a glass-fronted cabinet displays decorative items. Light streams through large windows, highlighting the warm wooden floor.
Home in Stamford
4.83 out of 5 average rating, 197 reviews

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.

Guest favourite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guesthouse in Waccabuc
4.98 out of 5 average rating, 125 reviews

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.

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.
Guesthouse in Greenwich
4.95 out of 5 average rating, 109 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, 191 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.

Top Guest favourite
A bright living area features a comfortable sofa set against a white wall, paired with a wooden coffee table. Large windows allow natural light to fill the space, while a patterned area rug adds warmth beneath. A modern chair and a small storage unit are also visible.
Cottage in Valhalla
4.96 out of 5 average rating, 329 reviews

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

When is the best time to visit Greenwich?

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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 $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!