Vacation rentals in Greenwich

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Top-rated vacation rentals in Greenwich

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

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Top 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, 129 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 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, 120 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 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
4.92 out of 5 average rating, 24 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 and crafted by a top-tier contractor. 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
A private deck is displayed with wooden planks, featuring a sun lounger and a small table with two chairs. A large umbrella provides shade, while trees can be seen in the background, enhancing the outdoor experience.
Cabin in Bell Haven
4.9 out of 5 average rating, 145 reviews

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.

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, 132 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

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, 59 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, 101 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.

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, 119 reviews

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

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, 103 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.

Guest favourite
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
4.84 out of 5 average rating, 190 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 balcony features a charming outdoor dining set with a table and two folding chairs. A spread of sliced bread, apples, and glasses of sparkling drink is arranged, overlooking a view of downtown Stamford, with a mix of buildings and greenery visible in the distance.
Apartment in Stamford
4.89 out of 5 average rating, 129 reviews

Honey Spot Studio | Downtown City Views

Enjoy a stylish experience at this centrally-located spot in the heart of downtown Stamford. Walk downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! 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.

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.

Popular amenities for Greenwich vacation 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 520 vacation rentals in Old Greenwich, 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.

  • 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 private suite rentals in Greenwich?

    Experience the best of Greenwich with our private suite rentals, starting at about $90 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.

  • Are there Greenwich bed and breakfast rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 bed and breakfast rentals with pools in Greenwich, available on Airbnb. Make a splash and soak up the sun in style!

  • 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 house rentals in Greenwich?

    Greenwich has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Greenwich

  • Total vacation rentals

    Explore 260 vacation rentals in Greenwich

  • Nightly prices starting at

    Greenwich vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 100 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    260 of Greenwich vacation 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!