The third-largest city in Connecticut, Stamford is an urban playground, which makes sense considering that it’s just a train ride away from New York City. Many of its attractions are anchored on it being a commercial hub, such as how the downtown area provides plenty of opportunities for shopping. Bedford Street is also a must-visit for shopaholics, and foodies will want to check out Harbor Point as well to try out the best of what the city has to offer in terms of food and drink. Stamford also brings people closer to nature via Cummings Beach, West Beach, and Cove Island. Book one of these luxury rentals in Stamford, Connecticut, to give yourself an opulent vacation in the city.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to luxury services and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Charming country house close to beaches and shops (from USD 465)
History buffs will love this home that was built in 1869. While it has been renovated and equipped with modern furnishings, it still retains the touches of its past. The house is big enough for 10 people, and it has an equally spacious backyard where your kids or pets can play around in.
The house also has a playroom, swing set, and game room, perfect if you’re traveling with kids, no matter the age. Greenwich’s beaches and shops are easily accessible from here.
Top guest reviews
Amenities & Room:
the play room was a total treat for the kidslots of space a huge yard kid-friendly and comfortableCleanliness:
the house was clean and beautifulthis house is very clean and xtra spaciouswe found the house very clean and in an excellent locationdierdre's property is tasteful very clean and spacious it is even better and more spacious that the picturesHost:
the home owners couldn’t be more welcoming and helpfulthe owner was very responsive and checked in to make sure we found everythingowners clearly take pride in their propertydeirdre is super responsive and made our stay totally comfortablethis is a wonderful property with a fantastic hostRead more reviewsLocation:
incredible home and great locationvery quiet and lovely neighborhoodlet me start with saying that i left a piece of my heart at this beautiful place
2. Sea Pearl (from USD 490)
Sea Pearl is just right for six people, making this a good choice for families or groups. This homey rental is a fantastic self-service rental, coming with a fully equipped kitchen so you can whip up your favorite meals. It has a balcony and patio where you can enjoy the surrounding views or the cool breeze. It also has speedy WiFi and is equipped with a smart TV.
This cozy home is close to West Beach, and the host throws in beach passes for you. This rental is pet-friendly and long-term guests are welcome here.
Top guest reviews
Amenities & Room:
the kitchen is small but easy to cook in with lots of light and equipmentHost:
cindy was a super accommodating hostRead more reviewsLocation:
super cute cottage close to the beachgood location for a walk to the beach areathis was a delightful little place in a great location with a well done backyard and interior
3. Beach home close to the downtown area of Stamford (from USD 415)
This tastefully decorated five-bedroom home, which sleeps 12, provides you with magnificent ocean views. You don’t have to wander far if you’re looking to entertain yourself, as the property comes with billiards, foosball, and ping pong equipment. Smaller kids, meanwhile, will enjoy playing other games or using the coloring books and other drawing materials provided by the host. There’s also a fire pit that you can use if you want to hang out in the yard.
This house is centrally located, putting you close to the downtown area, bus stop, train station, and beach. Pets are allowed here.
Top guest reviews
Cleanliness:
this house was so cozy everything was really clean and the area was central and safeHost:
the house was beautiful and elena was super quick & helpful with answering any questions we hadRead more reviewsLocation:
great location really appreciated the central ac during hot dayswe enjoyed being able to walk to cove beach
4. One-bedroom house with pool (from USD 472)
Zen House is a gorgeous property that is just right for two people, making this a fantastic choice if you’re planning to spend a holiday in Stamford with your significant other. The highlight of this property is its lap pool.
Want to make your holiday extra special? You can coordinate with the host and avail of the services of a housekeeper, chef, and even a masseuse.
Top guest reviews
Amenities & Room:
the bed was comfortable and there were lots of cozy places to sit with a bookHost:
olga and jose were wonderful hoststhe owner is exceptionally kind and thoughtfulolga and jose are wonderful attentive hostsolga is a caring conscientious and generous hostolga was very helpful and all of the instructions were clearRead more reviewsLocation:
this place was excellent for agetting away from things
5. Nautical-themed beach house (from USD 603)
Staying at this house will truly make you feel that you’re enjoying a beach holiday, and not just because it’s a few steps away from the beach. This rental, which can accommodate up to 11 people, has a nautical theme that encourages you to embrace your adventurous side.
A high chair and some toys are provided for families traveling with small children. Up to two dogs are allowed here.
Top guest reviews
Amenities & Room:
it's charming but up-to-date cozy but spacious and had everything we needed for a lovely staythe house is very comfortable and has a lot of room even for big familiesCleanliness:
everything is new clean and designed for your convenienceHost:
the owner victoria was very helpful and provided us with all the things that we neededvictoria was a wonderful host the property exceeded all expectations would love to stay againvictoria was helpful and very responsive with anything we neededshe’s responsive and informativewow such an amazing stay and victoria was an incredible hostRead more reviewsLocation:
this location was perfect for our family gathering over the holidaysbeing able to walk to the beach was great
6. Modern house with furnished backyard (from USD 698)
This accommodation is perfect for those who want to wind down by relaxing outside after a long day. The property has a spacious backyard with outdoor seating and a dining area, fire pit, and grill so you can kick back and relax as you enjoy the ocean breeze. If you’re traveling with kids, the property is equipped with a travel cot and a high chair. Fireplace and window guards are put in place to help keep your tots safe.
Do be aware that only those who are 25 years old and up are allowed to book this property.
Top guest reviews
Read more reviewsHost:
andrew & paula are great hostsandrew is a super host to the definitionandrew and paula were very kind to show us around the place and we enjoyed our trip very muchthe place was nice safe and andrew was a great hostandrew is very friendly you should check this place out
7. Eclectic home with opulent decor
Large enough to accommodate a dozen guests, this rental was built by the hosts in 2019. Its eclectic decors reflect their unique tastes, and each room has its own character. In the backyard, you’ll find a fire pit and hot tub, the latter of which you can request the host to set up for an additional fee.
If you enjoy cooking, you will appreciate the spacious kitchen. The house also has a game room that you can use to keep your party entertained.
Stamford, Connecticut, United States
8.72 km (5.5 mi) from Scalzi ParkAccommodates: 6
Top guest reviews
Amenities & Room:
a great place to entertain especially with kids with downstairs play room outdoor deck and fire pitthe fun decor and easy lay out made for a comfortable triphouse was very well decorated and comfortable for my group of fivewe played games at the large dining room table and were able to relax in the eveningsCleanliness:
very clean and comfortableeverything was clean and organizedclean cozy and thoughtfully organized placethe house is beautiful and cleangreat location clean and orderly very helpful communication with ownerHost:
the owners were available for questions throughout our stay and were extremely helpfulmichelle was a great host my family and i had an amazing time at her homemichelle and jd were very responsive and made us feel very welcomegreat space great hosts easy check injd and michelle have been very responsive and helpful throughout our entire stayRead more reviewsLocation:
this house is located in a very quiet neighborhood with a beautiful back yard surrounded by treeswe were co-workers in town for an event and this was the perfect locationwe used this serene location as a place to relax after going into nyc for the dayswe had a great holiday stay at michelle's placeit's definitely a perfect place to stay at for a fun peaceful getaway
8. Country home with garden (from USD 1495)
Stamford may be a highly urbanized city, but this rental, which is good for eight people, will make you feel as though you have traveled to the countryside, especially with the colorful garden framing the house.
This property has a game room equipped with a ping pong table and foosball. The house also has a theater and boasts of a good audio system throughout the house. The three fireplaces add a touch of romance to the property.
Top guest reviews
Cleanliness:
the home is perfect very comfortable clean and convenientRead more reviewsHost:
loved this house wes was a great hostand he was super communicative and helpful we would stay there again in a heartbeat
9. Waterfront home for 12
Built in 1920, this New England home allows you to enjoy views of the water right from the property. The beach is practically in your backyard, and the 100 ft (30 m) stretch of private beach will surely be the highlight of your holidays. You are even provided with equipment such as kayaks and paddleboards which you can use to maximize your stay by the waterfront. Similarly, bikes are available if you want to do your exploration off the water.
If you simply want to rest and relax on the property, you can take a nap on the hammock, sit around the fire pit, or have a barbecue as the sun sets. The interiors boast facilities including a music room and game room. It also has a business center in case you need to work during your holiday.
Stamford, Connecticut, United States
4.13 km (2.6 mi) from Scalzi ParkAccommodates: 12
Top guest reviews
Amenities & Room:
the house is well appointed with comfortable furniture throughoutthe view is espectacular and the house is very comfortablegreat house with beautiful sunrises and sunsets from the master bedroom and living roomthe sunrise from the bed was breathtaking and private beach was incredibleCleanliness:
the finishes/house is a bit older but the place was very cleanvery spacious house many rooms great for all sorts of occasionsHost:
she was a great hostcindy is one of my favorite hostsan amazing stay cindy was a great hostoutstanding accommodations host very warm and accommodatingcindy is also an excellent and responsive hostRead more reviewsLocation:
first the place was very ideally located right on the waterhighly recommend cindy's place we want to go back in the summercindy's place was perfect for a scenic stay in bridgeport
Treat yourself to an urban holiday
Stamford is dubbed as “the city that works”, but it doesn’t mean that it doesn’t have anything to offer to those who want to play. On the contrary, it has a lot in store for those who want to spend their holiday here, including cultural, dining, and sightseeing experiences. So plan your trip to Stamford today.
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