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 balcony is equipped with outdoor furniture, including two chairs and a small table. The scene is enhanced by a view of the city skyline during sunset, with soft, warm lighting reflecting off the buildings. Glasses are placed on the table.
Apartment in Stamford
4.94 out of 5 average rating, 241 reviews

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!

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, 62 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
4.98 out of 5 average rating, 125 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

Top Guest favourite
A cozy living room features a prominent stone fireplace, surrounded by soft, neutral furnishings. Natural light floods in through large windows, while wooden beams add rustic charm. A guitar rests next to a plush sectional sofa, inviting relaxation and comfort in a tranquil setting.
Home in Greenwich
4.97 out of 5 average rating, 60 reviews

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

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage combines rustic elegance with modern comfort. Relax by the stone fireplace, cook in the full kitchen, or step onto the river-facing deck to enjoy peaceful views. Outside, unwind in the heated pool or year-round hot tub, gather by the gazebo, or spot wildlife along the river. Utilize the fire pits and more. A tranquil retreat just 5 minutes from downtown Greenwich and 35 minutes from NYC.

Top Guest favourite
Apartment in Greenwich
4.95 out of 5 average rating, 102 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 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
4.93 out of 5 average rating, 27 reviews

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.

Top 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.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 108 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 room features warm hardwood floors and large windows allowing natural light. A king size bed is adorned with light bedding and soft pillows. A comfortable sofa can be seen in the background, alongside a wooden coffee table and plants, fostering a relaxed atmosphere.
Apartment in Stamford
4.94 out of 5 average rating, 53 reviews

Spacious. Water Views & Access. Steps to Beach.

Spacious apartment with King Size Bed. Direct access to Cove Pond & Long Island Sound. Easy access to downtown Stamford, Stamford Train Station & Manhattan. A few steps away from Cove Island Beach & Park. Apartment features high ceilings, central heating & cooling, brand new washer & dryer, hardwood floors, formal dining room and 60" HDTV with Amazon Fire TV. Guests have complimentary access to YouTube TV (comparable to cable), Peacock, & Prime Video.

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, 105 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.

Guest favourite
Guest suite in Bell Haven
4.93 out of 5 average rating, 14 reviews

Armada Suite Getaway

The space is located on the first floor, please use images for private access. Park in your assigned space at the orange cone and use the walkway to gain access through double door under deck with keyless entry. Inside you will find it includes a bed, TV, coffee maker, under counter fridge and other amenities. There is a deck, BBQ and outdoor shower to enjoy weather permitting .

Top Guest favourite
Home in West Side
4.99 out of 5 average rating, 184 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
4.81 out of 5 average rating, 144 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.

Popular amenities for Greenwich holiday rentals

When is the best time to visit Greenwich?

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Avg. price$309 NZD$274 NZD$300 NZD$323 NZD$362 NZD$392 NZD$385 NZD$374 NZD$364 NZD$374 NZD$371 NZD$388 NZD
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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 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 $69 NZD 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!