Holiday Homes in Stamford

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Featured Holiday Homes in Stamford and around

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
9.4 out of 10, Exceptional, (13)
"About 45min outside NYC, nice quiet neighborhood, motorcycle friendly, would absolutely stay here again. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is €125
includes taxes & fees
1 Oct - 2 Oct
Business or Weekend escape
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.2 out of 10, Wonderful, (15)
"We stayed here for one night & it was perfect! Husband is usually standoff-ish to “stay in someone’s house” but this bedroom/bathroom was completely private, including private fencing. The host sent us detailed information the day of regarding parking & misc info. TV in the room as well, so that was a perk. There’s also a keurig if you wanted to bring your own k-cups. Overall it was clean, simple, and way more promising than having stayed at a hotel for more space. Even the location it’s in was...
The price is €137
includes taxes & fees
30 Sept - 1 Oct
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, (13)
"This house was perfect for my group of 6 college friends. We hadn't gotten together in over 10 years and wanted to relax and catch up. The furniture and bedding were extremely comfortable, the kitchen had everything we could possibly need and more! Very spacious home with off-street parking for 6 cars. We loved it here!!! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (111)
"Property was perfect for our family. Gym, steam shower, and theatre room were all amazing. Effortless check in/check out process. Gorgeous home and neighborhood. Communication with our host Chris was easy and fast. Thank you for everything:) "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
10.0 out of 10, Exceptional, (3)
"Very comfortable home. Lots of space to spread out in. Location was ideal to our wedding venue. Home was as advertised. "
The price is €288
includes taxes & fees
30 Sept - 1 Oct
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Modern And Quiet Getaway
9.8 out of 10, Exceptional, (21)
"We had a great stay. Host was super friendly. Room was just as pictured and advertised. Quick Metro train available to get into the city in 30 minutes. Apartment was clean and there were all the things needed to cook if needed. Lovely home beautiful kept yard. Nice quiet neighborhood. 5 minute car or taxi ride to train station with ample parking available. We would recommended it! Thanks to the host for all the information provided. Lucio and Pilar"
Modern And Quiet Getaway
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (47)
"Wonderful stay. The home and town were a great location for our family trip!"
The price is €498
includes taxes & fees
1 Oct - 2 Oct
Captain's Cottage - Cold Spring Harbor Water Views
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (111)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Family-Friendly, Near-NYC Norwalk Retreat
2.0 star property
10.0 out of 10, Exceptional, (2)
"Met all of our expectations, made a very enjoyable stay with 2 little ones. Host was accommodating and went above and beyond to support our needs. "
The price is €484
includes taxes & fees
9 Oct - 10 Oct
Family-Friendly, Near-NYC Norwalk Retreat
Beautiful historic home in Stony Brook!
2.0 star property
9.0 out of 10, Wonderful, (4)
"The property was as described with a big and well equipped kitchen and also a large sized washer and dryer. The bathrooms are nicely renovated with every thing you might need. The location is very convenient and quick walk to Stony Brook Village. The bedrooms were well sized and as pictured. However, the beds could be a bit more comfortable. The two single beds squeaked a little bit. The property could also use a hair dryer and iron/ironing board. I brought those things with me but some others...
Beautiful historic home in Stony Brook!
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
2.0 star property
8.0 out of 10, Very good, (1)
"The apartment was clean, neat and most things looked new. AC was in windows. Dead end street and very quiet."
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (20)
"My friends and I stayed in Bridgeport for a weekend of music, and we had a great experience here! The owners were responsive and the place was exactly what we needed"
Cheerful 4 bedrooms residential house.
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (45)
"This house is beautiful and has everything you need, including a gorgeous view of the Sound. All communication was swift and easy. My family built some wonderful memories here this week!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Adorable Cottage with Water Views, Across the street from Prime & other eateries
10.0 out of 10, Exceptional, (59)
"We enjoyed our short stay at the cottage! The thoughtful amenities were appreciated (especially ALL your coffee needs except dairy, toiletries, filtered water ready in the fridge), and there were probably more we didn’t take advantage of…we were only there for 3 days and didn’t cook in the house but noticed the pantry was stocked with spices and cooking essentials. The beds and bedding were very comfortable. The outdoor area was lovely and well maintained but we didn’t use it much because of...
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Private entrance to this cozy first floor apartment in house. Close to transit.
9.2 out of 10, Wonderful, (5)
"The unit is centrally located on LI and very convenient! Anthony is a great host who is very accommodating! We would stay there again and again! The nearest LIRR is Hempstead"
Private entrance to this cozy first floor apartment in house. Close to transit.
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
9.0 out of 10, Wonderful, (22)
"Stay was absolutely wonderful, property was lovely and super easy to get to and from sleepy hollow. Definitely recommended."
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
9.6 out of 10, Exceptional, (14)
"We loved our little cottage, it was a perfect size for us. The backyard was a great space for our grandkids to run around in, which was fun for them as well. It was close to family so we could easily have them over for the day. The owners were very kid an responded quickly to our questions also. We also met some of the neighbors who were a lot of fun too!"
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (12)
"The house is huge and is very well equiped. Owners are very responsive to any questions or issues. Wonderful stay for the family."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
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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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Other property types in Stamford

Stamford Suites
2.5 star property
6.8 out of 10, (748)
"It was more than i expected. "
The price is €157
includes taxes & fees
11 Oct - 12 Oct
Stamford Suites
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (111)
"Property was perfect for our family. Gym, steam shower, and theatre room were all amazing. Effortless check in/check out process. Gorgeous home and neighborhood. Communication with our host Chris was easy and fast. Thank you for everything:) "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is €125
includes taxes & fees
1 Oct - 2 Oct
Business or Weekend escape
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.