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 favorite
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
4.92 out of 5 average rating, 131 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 favorite
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, 122 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
A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.
Apartment in Newburgh
4.84 out of 5 average rating, 346 reviews

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Top guest favorite
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

Top guest favorite
A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.
Apartment in Ossining
4.96 out of 5 average rating, 482 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Top guest favorite
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, 120 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)

Guest favorite
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 favorite
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.

Superhost
A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.
Guest suite in Wilton
4.8 out of 5 average rating, 240 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Guest favorite
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.

Top guest favorite
Home in West Side
4.99 out of 5 average rating, 181 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 favorite
Guesthouse in Southport
4.97 out of 5 average rating, 206 reviews

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.

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 € 35 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 & 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

  • Wi-Fi availability

    260 of Greenwich vacation 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!