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 dining area features a round wooden table set for four, surrounded by upholstered chairs. Natural light floods the space through large windows with simple drapes. A comfortable sofa and TV are positioned in the adjacent living area, complemented by modern lighting fixtures.
Apartment in Stamford
4.95 out of 5 average rating, 131 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
4.77 out of 5 average rating, 386 reviews

Flex Comfort Apts of Greenwich #2

Flex Comfort Apt #2 is 2 Bedroom / 1 Bath and sleeps 4. Apt #2 is the middle floor of a 3 apartment 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.

Guest favourite
The image displays a charming house constructed with blue siding, accompanied by a spacious wooden deck. A paved pathway lined with lights leads toward the structure, with outdoor seating and umbrellas visible, surrounded by a green lawn and shaded trees.
Cabin in Bell Haven
4.9 out of 5 average rating, 157 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 features a combination of comfortable seating arrangements, including sofas and armchairs. A coffee table sits in the center, surrounded by wooden floors. Natural light enters through multiple windows, creating a bright and inviting atmosphere. A dining table is visible in the background.
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
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.

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, 114 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.

Superhost
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
A private cottage entrance is framed by a sloped roof, featuring a large glass door complemented by a small window. Two modern chairs are positioned on the welcoming wooden deck, while a doormat adds a touch of practicality.
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.

Superhost
Apartment in Glenbrook
4.78 out of 5 average rating, 207 reviews

Downtown "Blue Nest" apartment

Cozy, adorable, updated and fully decorated 1 bedroom apartment in a downtown building with garage & 24 hours security. Equipped with everything you might need. Come stay with us and discover Stamford through the eyes of a local talented artist. There are certain things about the building that I can't change - please read the whole description before booking

Guest favourite
A bright kitchen is equipped with white cabinets and granite countertops. Stainless steel appliances include a dishwasher and oven. A small area rug lies on the hardwood floor, and utensils are arranged on the countertop near a window with natural light filtering through.
Apartment in Port Chester
4.97 out of 5 average rating, 104 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.

Top Guest favourite
Home in West Side
4.99 out of 5 average rating, 192 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
The exterior of the house is featured, showcasing a stone and gray siding facade with a charming arched wooden door. Lush greenery and ferns surround the entrance, while a stone pathway leads to the residence under a bright blue sky.
Cottage in Valhalla
4.96 out of 5 average rating, 330 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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Avg. price$252 AUD$223 AUD$245 AUD$263 AUD$295 AUD$319 AUD$313 AUD$305 AUD$297 AUD$309 AUD$309 AUD$311 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!