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Greenwich vacation rentals

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Top-rated vacation rentals in Greenwich

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Apartment in Stamford

4.82 out of 5 average rating, 146 reviews

Sunset Retreat: 1BR Walking Distance to the Beach

Welcome to our charming and spacious 1 bedroom Airbnb in the heart of the beach district in Stamford! This delightful 1st fl apartment offers everything you need for a memorable stay. Prime location offers the best of both worlds. Just a short 5-min stroll will take you to the local train station, providing easy access to neighboring cities and attractions. Additionally, downtown Stamford is a mere 7-min drive, where you can indulge in a wide array of dining, shopping, and entertainment options.

Mar 20 – 27

G$23,772 GYD per night

Apartment in Stamford

4.97 out of 5 average rating, 120 reviews

Sugar Shack Studio | Downtown Skyline Views

Location! Studio apartment located in the heart of downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and 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. This unique place has a style all its own!

Dec 19 – 26

G$29,265 GYD per night

Guesthouse in Norwalk

4.99 out of 5 average rating, 207 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

Aug 7 – 14

G$26,283 GYD per night

Apartment in Stamford

4.88 out of 5 average rating, 162 reviews

High-Line Harbor Flat 2BD|Train|HarborPoint Access

2 bedroom apartment in the Harbor Point area in Stamford, CT. Walking distance to the train station to NYC, restaurants, parks, shops & waterfront boardwalk. 5 minute drive to downtown. Bedrooms feature DWR memory foam mattresses (Sonno Prima) guaranteeing a great nights sleep. 40 inch Roku TV w live TV & access to hook up your favorite streaming services. The apartment is located on the third floor of a multi-family home and there are two flights of stairs to walk up to the apartment .

Dec 31 – Jan 7

G$28,154 GYD per night

Guesthouse in Norwalk

5.0 out of 5 average rating, 113 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

Jul 3 – 10

G$70,680 GYD per night

Guest suite in Greenwich

4.91 out of 5 average rating, 428 reviews

Charming Greenwich studio, 0.2 miles from train

A charming and spacious "studio" with private entry/exit and very close proximity to Cos Cob train station in Greenwich. Opens to a private back yard. Small library, stone walls, small desk, private hall and bath, and room for 2 (or 3) make it ideal for a weekend getaway with easy access to NYC, Port Chester, Stamford, and New Haven. Five minute walk to Cos Cob village for bakeries, juice and coffee shops, and restaurants. Kid-friendly. Air mattress or crib available upon request.

Jun 28 – Jul 5

G$42,341 GYD per night

Guest suite in Norwalk

4.9 out of 5 average rating, 111 reviews

Efficiency Garden Studio in South Norwalk, CT

Beautiful Efficiency Studio with private entrance in South Norwalk. Self-contained with private bath, kitchenette and off street parking. 10 min walk to South Norwalk Rail Station. 60 minutes to Manhattan, 10 min to historic SoNo. 10 min drive to Stamford. 5 minute drive to Merritt 7 and corporate business district. 5 minute to Norwalk Hospital. 5 min to City Hall. Close to all main arteries. Part of a quaint and charming arts & crafts bungalow, has separate entrance, very quiet.

Jul 29 – Aug 5

G$22,922 GYD per night

Home in Stamford

4.97 out of 5 average rating, 218 reviews

Midcentury Modern ZenHouse Sculptor Studio

Zenhouse mission to inspire creativity, art, spirituality and rejuvenate.Experience complete tranquility in the Zen-like environment .Please read house rules before booking . Zen House Satori consists of an architecturally significant mid-century modern 3.5 acre private estate -main house @ Zenhouse in CT. This is the ideal setting for a memorable romantic getaway, solo adventures and business travelers – not to mention photoshoots and film locations! Inside Sculptor studio

Nov 12 – 19

G$80,442 GYD per night

Apartment in Greenwich

4.79 out of 5 average rating, 355 reviews

The Safe House - High Tech Apt #3 - 4 beds

Comfortable and well stocked High Tech apartment delivers a great place to rest, work, and play. 2 Bedrooms (4 Beds) / 1 Bath. Features: Well stocked Eat in Kitchen. 55" Android smart TV with 300+ movie library on Google play, HBO, Netflix, and Hulu (w/ live TV). 3 x Work Stations with monitors, dock, and keyboard / mouse. 1 Mile from Greenwich Train station - 45 mins to Grand Central. Easy access to 95 and everything NY & CT have to offer. NO PARTIES OR EVENTS

Nov 30 – Dec 7

G$42,168 GYD per night

Loft in Stamford

4.96 out of 5 average rating, 161 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.

Sep 19 – 26

G$42,342 GYD per night

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Oct 17 – 24

G$17,656 GYD per night

Guest suite in White Plains

4.87 out of 5 average rating, 164 reviews

1BR close to White Plains train station

From NYC by train 40 minutes, and walking from my apartment to the train only 7 minutes, but coming back is uphill so takes longer. Convenient for shopping, and dining, and walking distance to downtown White plains. Please read the entire description, and make sure the place, you are looking for, before you reserve. Our apartments are completely renovated and have separate entrances. Please ask me a monthly rate.

Oct 7 – 14

G$28,944 GYD per night

Vacation rentals for every style

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Popular amenities for Greenwich vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Greenwich's top sights

Playland Park29 locals recommend

Westchester County Airport20 locals recommend

The Capitol Theatre22 locals recommend

Costco Wholesale6 locals recommend

Greenwich Point Beach28 locals recommend

The Performing Arts Center3 locals recommend

Other great vacation rentals in Greenwich

Home in Wilton

4.93 out of 5 average rating, 160 reviews

Mid Century Modern Cottage

Sep 23 – 30

G$29,606 GYD per night

Home in Stamford

4.98 out of 5 average rating, 210 reviews

Bright Stylish Chic 4BR 4BA Home

Jan 2 – 9

G$110,887 GYD per night

Home in Dobbs Ferry

4.92 out of 5 average rating, 306 reviews

Small cozy room in historic 1828 Dobbs Ferry home.

Jan 10 – 17

G$13,228 GYD per night

Guesthouse in Mahopac

4.96 out of 5 average rating, 107 reviews

Sunny Lakeview Guesthouse

Sep 6 – 13

G$26,304 GYD per night

Apartment in Mamaroneck

4.93 out of 5 average rating, 176 reviews

2 Bed/1 Bath Private Apartment in Mamaroneck

Mar 16 – 23

G$28,859 GYD per night

Guesthouse in Greenwich

4.88 out of 5 average rating, 82 reviews

Overlook Cabin in downtown Greenwich CT

Aug 27 – Sep 3

G$19,519 GYD per night

Guesthouse in Greenwich

5.0 out of 5 average rating, 19 reviews

Cozy brand new guest home

Jun 29 – Jul 6

G$29,952 GYD per night

Apartment in Greenwich

4.96 out of 5 average rating, 71 reviews

Cozy 2 BR Greenwich Apt. with easy access to NYC

Jun 7 – 14

G$36,060 GYD per night

Other great vacation rentals in Greenwich

Home in Greenwich

4.95 out of 5 average rating, 21 reviews

Cottage/Cabin Retreat by River Near Downtown

Jul 24 – 31

G$122,593 GYD per night

Guest suite in Stamford

4.97 out of 5 average rating, 36 reviews

Retreat in North Stamford

Jun 26 – Jul 3

G$29,561 GYD per night

Townhouse in Greenwich

4.91 out of 5 average rating, 97 reviews

Walk to Greenwich Ave [KING bed] BEST Location

Oct 11 – 18

G$112,262 GYD per night

Apartment in Stamford

5.0 out of 5 average rating, 52 reviews

Standalone Cottage surrounded by woods

Jan 19 – 26

G$22,752 GYD per night

Guest suite in Port Chester

4.96 out of 5 average rating, 84 reviews

Comfortable Colonial Urban retreat.

Jan 19 – 26

G$22,717 GYD per night

Home in Greenwich

4.82 out of 5 average rating, 62 reviews

Luxury designer home with garage in Greenwich

Dec 22 – 29

G$108,957 GYD per night

Guest suite in Wilton

5.0 out of 5 average rating, 34 reviews

Guest suite with private enter

Jul 10 – 17

G$20,075 GYD per night

Condo in Norwalk

4.95 out of 5 average rating, 19 reviews

*New Studio in the heart of Downtown Norwalk*

Oct 2 – 9

G$21,879 GYD per night

Quick stats about vacation rentals in Greenwich

Total rentals
280 properties
Rentals with dedicated workspaces
180 properties have a dedicated workspace
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
100 properties allow pets
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
9.4K reviews

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 60 vacation rentals in Purchase, over 340 vacation rentals in North Stamford, and over 50 vacation rentals in Tamarack Gardens.
Are there vacation rentals with a dedicated workspace in Greenwich?
Yes! Work meets play with ease at over 180 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.
Are there Greenwich vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Greenwich, available on Airbnb. Make a splash and soak up the sun in style!
Do condo rentals in Greenwich have air conditioning?
Absolutely! We offer over 10 condo rentals with air conditioning in Greenwich. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in bed and breakfast rentals in Greenwich?
Experience the best of Greenwich with our bed and breakfast rentals, starting at about $260 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.
Do bed and breakfast rentals in Greenwich have wifi?
Absolutely! We offer over 10 bed and breakfast rentals with wifi in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Greenwich have a bbq area?
Absolutely! We offer over 10 apartment 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 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore