
Holiday houses in Greenwich
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Top-rated holiday rentals in Greenwich
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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!

Greenwich abode Close to Just about Everything
2 - Bedroom apartment in a duplex. 4 - Minutes to Greenwich Avenue Shopping 6 - Minutes to Port Chester restaurants 8 - Minutes to Rye town and restaurants. 5 - Minutes to The Capital Theater 5 - Minutes to Byram Beach 10- Minutes to Tod's Point Beach 4 - Minutes by car to Greenwich and Port Chester Metro North Station 1 - Twin Air Mattress, SERTA auto inflate, 15inch raised {UPON REQUEST } Private and cozy retreat, steps away from one of Greenwich's Top Beaches - Byram Shore Beach Club.

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

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.

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

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.

The River Loft
Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

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.

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Captain's Cottage on Working Farm with Animals
Charming, fully renovated cottage with cathedral ceilings and private deck. Home has a separate queen bedroom, kitchen and living room on the main floor with small stove fireplace. There is a small loft on the 2nd floor with 2 twin beds accessed by a library ladder (note: no standing headroom in loft). Private outdoor deck with seating and BBQ. Fast wi-fi, laundry access and pet friendly.

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.

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
Stay near Greenwich's top sights
Other great holiday rentals in Greenwich

1Bd Cottage in Greenwich | Designer Stay near NY

Water view one bedroom

Cozy Cos Cob Studio

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

Waterfront Getaway - Norwalk, CT

Luxury Loft Apt. with easy access to NYC & CT

Solara – Luxury 1BR Downtown

Cozy Guest Suite in Greenwich, 1mi from train
When is the best time to visit Greenwich?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $253 AUD | $225 AUD | $246 AUD | $265 AUD | $297 AUD | $321 AUD | $316 AUD | $307 AUD | $299 AUD | $311 AUD | $311 AUD | $313 AUD |
| Avg. temp | 1°C | 2°C | 6°C | 12°C | 18°C | 23°C | 26°C | 25°C | 22°C | 15°C | 10°C | 4°C |
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 $57 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!
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