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Old Greenwich Vacation Rentals

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Our top choices for Old Greenwich vacation rentals

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is CA $277
CA $406 total
includes taxes & fees
Jul 29 - Jul 30
DUNE Fairfield Beach

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is CA $203
CA $335 total
includes taxes & fees
Jul 14 - Jul 15
Piermont Oasis

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (16 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is CA $306
CA $579 total
includes taxes & fees
Jul 6 - Jul 7
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (41 reviews)
"The location is beautiful and the hosts very amenable. Everything was clean, tidy and welcoming and there is a beautiful view out one of the bedroom windows to the lake in the back. I can highly recommend this destination and look forward to staying here again on a return trip!"
United States
Anonymous traveller
The price is CA $268
CA $494 total
includes taxes & fees
Jul 14 - Jul 15
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is CA $312
CA $591 total
includes taxes & fees
Jul 5 - Jul 6
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is CA $922
CA $1,243 total
includes taxes & fees
Jul 5 - Jul 6
Spacious 3BR Luxe Escape near NYC

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is CA $172
CA $467 total
includes taxes & fees
Jul 7 - Jul 8
Stamford Hideaway w/ Fire Pit

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Bronx
9.8 out of 10, Exceptional, (26 reviews)
"Great sunny spacious and clean apartment for us to stay in when visiting family nearby. The hosts were super responsive whenever we had questions, and made our stay super seamless. Would definitely stay here again the next time we’re in town!"
United States
Lauren A.
The price is CA $257
CA $610 total
includes taxes & fees
Jul 5 - Jul 6
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (80 reviews)
"Location was perfect!"
United States
Linda J P.
The price is CA $546
CA $1,010 total
includes taxes & fees
Aug 3 - Aug 4
Captain's Cottage - Cold Spring Harbor Water Views

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is CA $223
CA $409 total
includes taxes & fees
Jul 6 - Jul 7
Spacious Studio with Pool Table

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
9.8 out of 10, Exceptional, (8 reviews)
"We had such a nice and peaceful stay! Shelton’s place was super clean, quiet, comfortable, and had everything we needed. Would definitely stay here again! "
United States
Katie M.
The price is CA $217
CA $514 total
includes taxes & fees
Jul 23 - Jul 24
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is CA $277
CA $545 total
includes taxes & fees
Jul 5 - Jul 6
Luxe Provincial Style Studio w/ Patio & Parking

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is CA $204
CA $448 total
includes taxes & fees
Jul 14 - Jul 15
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is CA $204
CA $595 total
includes taxes & fees
Jul 9 - Jul 10
Modern Luxe 1BR Apt in Downtown Stamford

Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
The price is CA $269
CA $446 total
includes taxes & fees
Jul 19 - Jul 20
Welcoming 1 bedroom apartment in beautiful harbor village.

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is CA $134
CA $191 total
includes taxes & fees
Jul 6 - Jul 7
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
9.0 out of 10, Wonderful, (12 reviews)
"Had a great stay "
United States
Desiree
The price is CA $150
CA $247 total
includes taxes & fees
Jul 22 - Jul 23
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is CA $291
CA $562 total
includes taxes & fees
Jul 8 - Jul 9
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (8 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is CA $262
CA $528 total
includes taxes & fees
Aug 3 - Aug 4
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is CA $149
CA $200 total
includes taxes & fees
Jul 6 - Jul 7
2-bedroom apartmet No cleaning Fee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Old Greenwich Hotel Reviews

Find out more about Old Greenwich

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Old Greenwich. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Old Greenwich?

Yes, we offer vacation rentals close to well known points of interest in Old Greenwich, or you can go with a more remote option if you want a relaxing place to stay. Visitors like the top-notch restaurants and shops in Old Greenwich. Make sure you have time to check out the beaches and cafes during your trip.

What are some of the best vacation rentals in Old Greenwich?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental near Old Greenwich is equipped with a garden, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Old Greenwich?

Expedia has 13 vacation rentals for your stay in Old Greenwich.

What can I see and do in Old Greenwich?

Greenwich Point Park and Rosa Hartman Park are a couple of lovely local spots to get outside and enjoy nature. Commerce Park and Dundee Woods are other places to visit while you're in town.

What are vacation rentals like in Old Greenwich?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Old Greenwich. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.