Trips to Stamford

There are a lot of options in Stamford. If you plan on staying in the Stamford area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Stamford:

• Studio Flat Above Historic Cider Mill
• Family-Friendly 2BR with Parking Near NYC + Hospital
• Charming Cottage located on Historic Estate 1 Hour from NYC!
• New Beach Home near Stamford Downtown/Shippan
• 2BR Flat above Historic Cider Mill
• Mid Century Modern ZEN House with Pool. 50 min from New York City
• Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.
• 4 BR Classic Country House in CT
• Westport Gem - walk to shops, dining, town center, pet-friendly
• Boutique Stay 2C in Heart of Downtown

There are 57 vacation rentals with private pools near Stamford. Top-rated homes that have access to a swimming pool include:

• Westport Luxury Family Retreat | Resort Pool Debuting July 2026
• Modern Apt Close to Downtown
• Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach
• Back Country Estate w/Pool, Sleeps 8 - Fully loaded, Pet Friendly Greenwich CT

If you are looking for a family-friendly vacation home in Stamford, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Stamford:

• Cozy 2br apartment in Greenwich with driveway. Walk to restaurants & beach!
• Luxurious 1BR Downtown Stamford
• Family Cottage with 4 King Beds

Currently, the total number of properties listed in 2026 is over 788 in the Stamford area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Stamford.