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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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, 133 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
The cabin's entrance is framed by lush greenery and flowering plants. A wooden walkway leads to the door, and a small set of steps offers access. The rustic exterior features dark wood siding and a window for natural light.
Guest suite in Fire Island Pines
4.96 out of 5 average rating, 103 reviews

Fire Island Pines: Studio Cabin

Studio cabin (approx. 13.5 x 15 ft.) Functional, basic, rustic, atmospheric—It's just a little cabin in the woods. The shack can accommodate only 2 people max. Queen bed (sheets, blankets) Bathroom (shower/towels) Kitchenette (fridge, microwave, sink, dishwasher, dishes, cutlery, glasses) A/C (window unit) Fan Basic tv Internet Beach chairs/umbrellas, Outside shower The Pines is primarily a gay community, but welcoming to all. We love our wild deer and squirrels but no pets in the cabin

Superhost
Apartment in Greenwich
4.75 out of 5 average rating, 401 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
Home in Byram
4.94 out of 5 average rating, 36 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, 106 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
A modern kitchen is characterized by wood and gray cabinetry, featuring stainless steel appliances and a spacious countertop. Natural light floods the area through a skylight and a window, with a small dining table placed against the wall, enhanced by a collection of kitchenware on display.
Loft in Harbor Point
4.93 out of 5 average rating, 226 reviews

Luxury Loft Apt. with easy access to NYC & CT

Gorgeous and modern 2 bedroom apartment in Harbor Point area. Walking distance to the train station , restaurants, parks, shops, waterfront boardwalk and just 48 minutes from the Big Apple. Few minutes drive to downtown. A large kitchen and laundry with everything you may need and a spacious living room with 48 inch TV cable access and internet.The apartment is professionally cleaned & sanitized up to CDC guidelines & inspected before each stay to ensure your safety.

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, 118 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
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
4.9 out of 5 average rating, 137 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, 112 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.

Superhost
Guest suite in Greenwich
4.64 out of 5 average rating, 22 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
A cozy living room features a large sectional sofa adorned with decorative pillows. A glass coffee table sits on a soft area rug, while a flat-screen TV is mounted on the wall. Two windows allow natural light to fill the space, enhancing its inviting atmosphere.
Apartment in Port Chester
4.97 out of 5 average rating, 109 reviews

Sunny & Cozy Stay by Capitol Theatre/Downtown

Within walking distance of downtown Port Chester, Capitol Theatre, Metro North, and so much more; this 2 bedroom apartment with PRIVATE ENTRANCE provides a comfortable, inviting stay for those visiting the New York City/Metropolitan area. We are centrally located near the I-287, I-95, so commuting to and from the area is easy.

Popular amenities for Greenwich holiday rentals

When is the best time to visit Greenwich?

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Avg. price$253 AUD$225 AUD$246 AUD$264 AUD$297 AUD$321 AUD$315 AUD$306 AUD$298 AUD$311 AUD$311 AUD$312 AUD
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Frequently Asked Questions

  • What are the best places to stay in Greenwich?

    Greenwich has stays ranging from historic homes near downtown, modern apartments close to the waterfront, and quiet retreats in neighboring residential areas. Many listings welcome families, groups, and pets, making it easy to find accommodations that suit your needs.

  • What are the best things to do in Greenwich with kids?

    Families often explore the Bruce Museum for interactive exhibits, enjoy sandy play at Greenwich Point Park, and stroll through scenic gardens at the Montgomery Pinetum. Outdoor spaces and educational centers make Greenwich welcoming for young visitors.

  • What are some of the best things to do in Greenwich?

    Greenwich has art galleries, historic estates, and waterside parks for relaxing strolls. Visitors frequently suggested stops include the Bruce Museum, Greenwich Point Park, and the downtown district lined with shops and cafes.

  • How is the weather in Greenwich?

    Greenwich has cold winters near 29–40°F (-2–5°C), mild spring weather around 36–61°F (2–16°C), and warm summers from 66–86°F (19–30°C). Rainfall is steady throughout the year, so packing layers and a waterproof jacket is often suggested.

  • When is the best time to visit Greenwich?

    Late spring and early fall are frequently suggested for comfortable temperatures and outdoor activities. Summer attracts visitors for beach outings and community events, while winter appeals to those who enjoy quieter streets and indoor cultural sites.

  • What are the best places to visit in Greenwich?

    Explore the Bruce Museum for art and science exhibits, relax at Greenwich Point Park with coastal scenery, and wander through the gardens at Montgomery Pinetum. Downtown Greenwich has local shops and spaces to experience community life.

  • What are some hiking trails in Greenwich?

    Locals often enjoy walking woodland paths at Montgomery Pinetum, strolling the trails around Byram Park, and exploring the nature centers near Mianus River Park. The area's preserves and parks welcome hikers of all skill levels.

  • What are some family activities we can do in Greenwich?

    Families can explore interactive exhibits at the Bruce Museum, participate in outdoor play at Greenwich Point Park, and attend workshops at local community centers. Gardening programs and art classes are frequently suggested for kids.

  • What are some of the best day trip ideas from Greenwich?

    Many visitors plan day trips to nearby coastal towns, art museums, and nature reserves around the region. You might explore larger city attractions, historic villages, or scenic parks just outside Greenwich.

  • Are there any pet friendly accommodations available in Greenwich?

    Greenwich has a range of pet friendly rentals, especially in residential neighborhoods and around the waterfront. Some local parks welcome dogs, making it easier to enjoy outdoor activities with your pet.

  • What are some local tips for visiting Greenwich?

    Greenwich locals often suggest exploring both waterfront and inland neighborhoods, trying fresh seafood in casual eateries, and visiting during weekdays for quieter shopping and museum experiences. Comfortable walking shoes and weather-appropriate layers are useful throughout the year.

  • What is Greenwich known for?

    Greenwich is known for its historic estates, arts and cultural institutions, and coastal parks. The town has a strong maritime heritage, vibrant downtown shops, and a mix of residential and scenic landscapes.

  • What are the best hidden gems to explore in Greenwich?

    Explore the garden paths at Montgomery Pinetum, visit smaller art galleries near downtown, and discover quiet stretches of beach at local parks. Neighborhood farmers markets and historic cemeteries offer glimpses of local culture not always on typical itineraries.

  • What are the best foods to try in Greenwich?

    Greenwich has fresh New England seafood, Italian-inspired dishes, and farm-to-table salads. Locally baked pastries and artisanal ice cream are often suggested treats near the waterfront and downtown cafés.

  • What should I bring for a trip to Greenwich?

    Pack comfortable walking shoes, a waterproof jacket, and layers suited to seasonal temperatures. If planning outdoor activities, sunscreen and reusable water bottles are helpful; a camera can capture scenic views in parks and along the coast.

  • What is the nightlife in Greenwich like?

    Nightlife in Greenwich has wine bars, contemporary restaurants, and occasional live music performances. The downtown area is known for low-key venues and spaces to gather with friends for drinks or conversation.

  • What are the most popular events or festivals in Greenwich?

    Seasonal outdoor festivals, art fairs, and local farmers markets are frequently suggested in Greenwich. The town hosts community events near the waterfront and cultural gatherings, especially in late spring and summer.

  • Are there family friendly vacation rentals in Greenwich?

    Greenwich has family friendly vacation rentals in residential areas, as well as near parks and downtown shopping districts. Many spaces include amenities for children, making it easy for families to explore together.

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 $56 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!