
Vacation rentals in Greenwich
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Top-rated vacation rentals in Greenwich
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Ranch in the Woods | A Peaceful Designer Retreat
Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

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

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

Get Away to "Hygge" Tiny House on 75 Private Acres
Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, propane bbq grill, dining table/chairs, fire pit. Lawn games available on request.

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.

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.

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. $19 cleaning with or without pets.

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.

A Lovely Cottage in the Woods (Pool Open May 8!)
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.

The Treecastle at the Roundhouse Homestead
The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Viridian House
This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.
Popular amenities for Greenwich vacation rentals
Stay near Greenwich's top sights
Other great vacation rentals in Greenwich

Close to New York City-Old Greenwich Surf Shack II

The Cottage in Greenwich

The Port Chester's star

Walk to Greenwich Ave and Train

Modern Tranquil Home In Connecticut- 40 min to NYC

Great hotel alternative, near Greenwich train stn

Waterfront Getaway - Norwalk, CT

Parkside Greenwich Retreat
When is the best time to visit Greenwich?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$42,053 GYD | G$42,890 GYD | G$43,517 GYD | G$39,124 GYD | G$43,936 GYD | G$47,493 GYD | G$46,656 GYD | G$45,400 GYD | G$44,145 GYD | G$46,028 GYD | G$46,028 GYD | G$46,237 GYD |
| 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 vacation rentals in Greenwich

Total vacation rentals
Explore 260 vacation rentals in Greenwich

Nightly prices starting at
Greenwich vacation rentals start at G$8,369 GYD per night before taxes and fees

Verified guest reviews
Over 11,660 verified reviews to help you choose

Family-friendly vacation rentals
140 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 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!
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