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Vacation Homes in Old Greenwich

Our top choices for Old Greenwich vacation homes

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

10.0 out of 10, Exceptional, (1)
"My wife, little one and I needed a place to stay to attend a wedding at “The Mansion at Oyster Bay”. The space was well kept, comfortable, and very conveniently located. The hosts were present at check in and very communicative throughout our stay. We had a little hiccup and they handled it very well. I highly recommend staying at Yvonne and Michael’s house. "
The price is ¥19,102
¥28,707 total
includes taxes & fees
Sep 8 - Sep 9
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

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

8.0 out of 10, Very Good, (16)
"Great place great location"
The price is ¥13,886
¥19,814 total
includes taxes & fees
Aug 27 - Aug 28
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

The price is ¥21,159
¥29,786 total
includes taxes & fees
Sep 7 - Sep 8
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is ¥22,746
¥44,085 total
includes taxes & fees
Sep 3 - Sep 4
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

3-bedroom apartment with AC in Great Neck

The price is ¥15,737
¥34,460 total
includes taxes & fees
Sep 5 - Sep 6
3-bedroom apartment with AC in Great Neck

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

10.0 out of 10, Exceptional, (1)
"I chose this apartment for its location primarily and it was a hit. Since we were traveling and staying for two weeks with a toddler and a new baby I was looking for it to also have an outdoor space, and it was wonderful as seen in the pictures. For personal reasons I had to change my dates a few days before my booking was coming up, the hosts had no problem to accommodate my needs. During our stay, we even had the opportunity to meet the neighbor next door and visit her garden. The neighborhood...
The price is ¥24,980
¥47,394 total
includes taxes & fees
Sep 8 - Sep 9
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is ¥42,466
¥90,897 total
includes taxes & fees
Sep 3 - Sep 4
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
The price is ¥25,715
¥52,348 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

45 Minutes from NYC, Entire House near Stamford Downtown,

10.0 out of 10, Exceptional, (13)
"Ana has thought of everything! The home was stocked with everything we needed. It made our stay amazing!"
The price is ¥37,029
¥68,812 total
includes taxes & fees
Aug 26 - Aug 27
45 Minutes from NYC, Entire House near Stamford Downtown,

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

9.0 out of 10, Wonderful, (2)
"the home was nice clean if in the area I would stay here again"
The price is ¥33,796
¥73,984 total
includes taxes & fees
Aug 28 - Aug 29
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
The price is ¥88,017
¥113,016 total
includes taxes & fees
Aug 26 - Aug 27
3BR Prime Luxury near NYC w Arcade Room

Live the luxury lifestyle 2 bedroom 2 bathrooms Pool, private massage downtown

2.0 star property
The price is ¥28,212
¥36,558 total
includes taxes & fees
Sep 15 - Sep 16
Live the luxury lifestyle 2 bedroom 2 bathrooms Pool, private massage downtown

Peaceful 5 Bedroom 3 Bathroom House - 30 min from NYC

9.4 out of 10, Exceptional, (8)
"Lots of sleeping and common space. Super easy to work with the owner."
The price is ¥23,143
¥112,513 total
includes taxes & fees
Aug 28 - Aug 29
Peaceful 5 Bedroom 3 Bathroom House - 30 min from NYC

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

10.0 out of 10, Exceptional, (4)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
The price is ¥33,062
¥62,118 total
includes taxes & fees
Sep 1 - Sep 2
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Cheerful Home in Yonkers NY

7.6 out of 10, Good, (4)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
The price is ¥36,735
¥87,031 total
includes taxes & fees
Aug 31 - Sep 1
Cheerful Home in Yonkers NY

Family getaway.Commuter's Dream.Weddings&Events.Content House.Luxury Smart Home

10.0 out of 10, Exceptional, (1)
"Wow! I wish we could have stayed here more than just one night! The host was so accommodating of our last-minute reservation and provided friendly and thoughtful assistance throughout our stay. This home is stunning! Careful planning and top-of-the-line finishes clearly went into every detail of this beautiful family home and we were so comfortable in every space. Larchmont train station is just steps away and made our travel to NYC a breeze. The home truly has a park-like feel and the house is...
The price is ¥198,369
¥282,632 total
includes taxes & fees
Aug 31 - Sep 1
Family getaway.Commuter's Dream.Weddings&Events.Content House.Luxury Smart Home

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (66)
"Great home to stay. Beautiful area to explore!"
The price is ¥41,878
¥85,452 total
includes taxes & fees
Sep 1 - Sep 2
Captain's Cottage - Cold Spring Harbor Water Views

Gorgeous Apt w Harbor Views & Gym

The price is ¥32,327
¥100,728 total
includes taxes & fees
Sep 12 - Sep 13
Gorgeous Apt w Harbor Views & Gym

Charming Long Island Family Getaway with Pool. An hour from Hamptons

7.6 out of 10, Good, (7)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is ¥79,215
¥180,150 total
includes taxes & fees
Sep 6 - Sep 7
Charming Long Island Family Getaway with Pool. An hour from Hamptons

The West Lane Inn - Queen Room

9.4 out of 10, Exceptional, (3)
"Vert nice property, very nice and accommodating proprietor and staff."
The price is ¥54,919
¥61,972 total
includes taxes & fees
Aug 27 - Aug 28
The West Lane Inn - Queen Room
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