Holiday Rentals in Stamford, CT

526 available vacation rental offers

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Stamford, CT holiday rentals
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Best Holiday rentals and Airbnb offers in Stamford, CT

Find the Best Seaside Holiday Rentals in Stamford, CT

Experience relaxing coastal vibes at seaside holiday rentals in Stamford, CT, positioned short distances from local beach-town shorelines.

Close To New York City-old Greenwich Surf Shack Ii - Stamford, CT
9.6 38 reviews

Close To New York City-old Greenwich Surf Shack Ii

apartment, Greenwich
This charming one-bedroom apartment is located in Old Greenwich, a picturesque coastal district just 1.6 kilometres from Connecticut's best sound beach and 80 kilometres from Grand Central Terminal in Manhattan. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The flat can comfortably accommodate up to four guests with a bedroom, living room with a pull-out sofa and futon, a loft with a single bed, and a separate yard area with patio furniture. Guests can enjoy a range of amenities including free guest passes and parking to Greenwich Beaches & Islands, along with bicycles, and a well-equipped kitchenette.
325 M² House ∙ 5 Bedrooms ∙ 8 Guests - Stamford, CT
No reviews

325 M² House ∙ 5 Bedrooms ∙ 8 Guests

house, Stamford
House for up to 8 people. You will be in Stamford.
Services and facilities include an iron, free parking and an access for persons with reduced mobility. This house also has a terrace!
Beach House In Old Greenwich, Ct - Stamford, CT
No reviews

Beach House In Old Greenwich, Ct

apartment, Greenwich
This apartment is situated in a peaceful family-friendly neighbourhood, close to the popular Tod's Point/Greenwich Point beach and a short walk from the town centre. The property is conveniently located for exploring Greenwich and its surrounding areas, with easy access to public transport.
The spacious apartment is located in a 100-year-old house and offers a generous 371 square metres of living space, with four bathrooms, a fully equipped kitchen, a playroom, and an au pair suite. Guests can enjoy a range of amenities, including a private garden, a terrace, a fitness centre, a spa, and a dedicated play area for children.
Boutique Stay 2c In Heart Of Downtown - Stamford, CT
9.9 105 reviews

Boutique Stay 2c In Heart Of Downtown

apartment, Greenwich
This charming one-bedroom flat is located in the heart of Greenwich, just a short walk from the train station and the shops and restaurants of Greenwich Avenue. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The 51 square metre flat can comfortably accommodate two guests. It offers a well-equipped kitchen, a dedicated workspace, a private entrance, and access to shared laundry facilities.

Best family friendly Stamford, CT holiday rentals

Among the 526 accommodations in Stamford, CT, here are the 4 best family friendly rentals

Family-friendly Stamford Downtown Delight - Stamford, CT
10 1 review

Family-friendly Stamford Downtown Delight

apartment, Stamford
This Stamford apartment, conveniently located an 11-minute walk from the Stamford Centre for the Arts and a 15-minute walk from Stamford Town Centre, offers easy access to the town's cultural attractions.
The 177 square metre (1907 square foot) property boasts a spacious four-bedroom, three-bathroom layout sleeping eight, complete with a fully equipped kitchen, in-unit laundry, free Wi-Fi, and on-site parking.
Greenwich Luxe Residence Retreat W/ Parking & Wifi - Stamford, CT
No reviews

Greenwich Luxe Residence Retreat W/ Parking & Wifi

apartment, Greenwich
This Cos Cob flat is situated conveniently close to downtown amenities and the Metro-North train station, offering straightforward access to Greenwich attractions.
This one-bedroom flat accommodates up to four guests and features a custom kitchen with top-brand appliances, a rooftop garden with city views and an electric grill, secure off-street parking, and in-unit laundry, with optional access to a wellness spa.
Historic 6-bdrm Tudor Estate W Pool/tennis Access - Stamford, CT
9.6 10 reviews

Historic 6-bdrm Tudor Estate W Pool/tennis Access

apartment, Stamford
This six-bedroom apartment is ideally located in central Stamford, just a short walk from both E. Gaynor Brennan Golf Course and Stamford Hospital. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious flat is perfect for large groups or families, offering a comfortable and well-equipped living space. Guests can enjoy a range of amenities, including a swimming pool, tennis court, sauna, and barbecue facilities, as well as a fully-equipped kitchen, a terrace, and a garden.
Modern & Comfortable 3br Stay, Close To Everything - Stamford, CT
9.7 314 reviews

Modern & Comfortable 3br Stay, Close To Everything

apartment, Stamford
This Stamford apartment is situated in a residential area, just a short walk from Elm Street's diverse restaurants and within easy reach of the city centre, the I-95 motorway and the Metro North train station, providing convenient access to Manhattan (35 minutes by train). The apartment consistently receives excellent ratings for its location, cleanliness and user experience.
The apartment has a well-equipped kitchen with modern appliances, a comfortable living area with a flat-screen TV and a cosy bedroom with a queen-size bed and ample storage space. Guests can enjoy a shared patio and backyard, a fitness centre, high-speed Wi-Fi and the convenience of Alexa smart home technology.

Frequently asked questions about holiday rentals in Stamford, CT

  • What should a first-time visitor not miss in Stamford, CT?

    You should definitely visit the Stamford Museum & Nature Center, it's a great place to learn about the local history and natural world. And if you're interested in the arts, the Stamford Center for the Arts is a must-see.
  • What are the best Airbnb and holiday rentals in Stamford, CT?

  • Which neighborhood in Stamford, CT should you consider for a vacation rental?

    The downtown area is a popular choice for vacation rentals, as it's close to the action and has lots of restaurants and shops. If you're looking for something quieter, the Springdale neighbourhood is a nice option, with its charming streets and parks.
  • What are the most popular Airbnbs in Stamford, CT?

  • What are the top family-friendly attractions in Stamford, CT?

    The Stamford Museum & Nature Center is a great choice for families, with its interactive exhibits and outdoor trails. The Mill River Park is also a popular spot for families, with its playground, splash pad, and amphitheatre.
  • What are the best holiday rentals with a pool in Stamford, CT?

    Harborview/freeparking/downtown, Lux 1br W/ Amenities Downtown and Stamford Grand Apartment + Cozy Den are the best holiday rentals with a pool in Stamford, CT.

  • When is the best time to book a vacation rental in Stamford, CT?

    The best time to book a vacation rental in Stamford is during the shoulder seasons, from April to May or September to October, when the weather is still pleasant but the crowds are smaller.
  • What are the best rentals for families and kids in Stamford, CT?

  • What are the best budget-friendly activities in Stamford, CT?

    Take a walk or cycle along the scenic waterfront, visit the free exhibits at the Stamford Museum & Nature Center, or enjoy a picnic in Mill River Park.
  • What are the best rentals or Airbnbs with a jacuzzi in Stamford, CT?

  • What are the best restaurants with local dishes in Stamford, CT?

    For a taste of local seafood, try the Lobster Shack at the Harbor. If you're looking for something more casual, the Elm Street Oyster House is a great option.
  • What are the best walking or cycling routes in Stamford, CT?

    The Stamford Town Green is a popular spot for a stroll, and the nearby Mill River Park offers scenic walking and cycling trails. The Cove Island Park is another great option for walking and cycling, with its beautiful views of Long Island Sound.
  • Are there pet-friendly attractions in Stamford, CT?

    Mill River Park is a great place to take your dog for a walk, and many restaurants in Stamford have outdoor seating that is pet-friendly.
  • What are the benefits of choosing a vacation rental in Stamford, CT?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities such as kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Stamford, CT?

    The Stamford Sports Center is a popular destination for sports enthusiasts, offering a variety of activities such as ice skating, swimming, and basketball. The Stamford High School Stadium is also a popular venue for sporting events.

Popular destinations

Discover Self-Catering Rentals with a Pool in Stamford, CT

Our holiday rentals near the water in Stamford, CT include a pool, so a relaxing swim is always on the cards.

Private Luxury Apt With Gym - Stamford, CT
No reviews

Private Luxury Apt With Gym

apartment, Stamford
This Stamford city centre flat is ideally located near the train station, providing easy access to shops, restaurants and cultural attractions such as the Palace Theatre and Stamford Museum & Nature Centre.
The 64 square metre apartment offers one bedroom, one bathroom, and sleeps three, boasting a modern kitchen with dishwasher and microwave, plus access to a swimming pool and fitness centre within the building.
Stamford Waterfront Retreat - Stamford, CT
No reviews

Stamford Waterfront Retreat

apartment, Stamford
This centrally located Stamford flat offers convenient access to shopping and entertainment, being a 3-minute drive from Stamford Town Centre and the Stamford Centre for the Arts, and a 12-minute walk from Stamford's Metro-North train stations.
This 69 square metre, one-bedroom flat accommodates up to three guests and features a well-equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, and access to shared amenities including a swimming pool and fitness centre.
Modern Apt Close To Downtown - Stamford, CT
No reviews

Modern Apt Close To Downtown

apartment, Stamford
This two-bedroom flat is situated in Stamford's town centre, offering direct access to shops and arts venues, and is a seven-minute walk from Stamford train station, providing easy regional travel.
Spanning 97 square metres, this apartment accommodates up to five guests and features a fully equipped kitchen, air conditioning, on-site swimming pool, fitness centre, and a pool table for entertainment.
Downtown Stamford Apt | Walkable Location - Stamford, CT
No reviews

Downtown Stamford Apt | Walkable Location

apartment, Stamford
This centrally located Stamford flat offers direct access to Metro North train services and is a short walk from downtown Stamford's dining and shopping.
This two-bedroom, two-bathroom flat accommodates up to five guests and features a resort-style outdoor swimming pool, a 465 square meter fitness centre with yoga facilities, a billiard room, and an on-site theatre.

Top-Rated Self-Catering Holiday Rentals with Free Parking in Stamford, CT

Driving to Stamford, CT? These holiday rentals include a car park, making it simple to reach the coast and local beaches.

Harbor Haven, Apt #2, 2 Br/1ba - Stamford, CT
No reviews

Harbor Haven, Apt #2, 2 Br/1ba

house, Stamford
This South End apartment offers convenient access to educational institutions, situated 17.7 kilometres from SUNY Purchase, 19.3 kilometres from Manhattanville College, and 28.9 kilometres from Iona College, with Westchester County Airport 17.7 kilometres away.
This air-conditioned flat accommodates up to seven guests and features a kitchen with a fridge and microwave, alongside a dedicated seating area for relaxation.
Beautiful Home Residential Area - Stamford, CT
8.8 19 reviews

Beautiful Home Residential Area

apartment, Stamford
This four-bedroom house in Stamford's Glenbrook district offers a quiet residential setting, located approximately 1.3km from the town centre and a 0.8km walk from the train station.
The property sleeps eight guests, features a kitchen, air conditioning, parking, and internet access, and is near amenities including a fitness centre and shops.
Peaceful, Sunny Apartment In Downtown Stamford - Stamford, CT
10 2 reviews

Peaceful, Sunny Apartment In Downtown Stamford

apartment, Stamford
This one-bedroom flat in Downtown Stamford offers a prime location, just a short walk from local eateries and entertainment, with straightforward access to New York City.
This modern apartment accommodates two guests and features a fully equipped kitchen, air conditioning, an onsite gym, and free parking, with a Smart TV for your enjoyment.
Charming Beach House  Walk/bike To Town & Beach! - Stamford, CT
No reviews

Charming Beach House Walk/bike To Town & Beach!

apartment, Greenwich
This Old Greenwich property is situated within walking distance of Old Greenwich's shops and restaurants, a short cycle ride (approximately 1.6km) from Old Greenwich beach and its amenities, and less than an hour by train from New York City.
The four-bedroom, three-bathroom house sleeps seven, offering a well-equipped kitchen, home gym, a large garden with family amenities including bikes and a trampoline, plus bi-weekly cleaning during your three-week stay.

Find the Best Luxury Holiday Rentals in Stamford, CT

Upscale luxury holiday rental or Airbnbs in Stamford, CT offer a refined stay you will want to return to, featuring premium amenities throughout.

Welcome To Darien - Stamford, CT
No reviews

Welcome To Darien

apartment, Darien

Best Stamford, CT holiday rentals with a balcony

Midcentury Modern Zenhouse Sculptor Studio - Stamford, CT
9.7 3 reviews

Midcentury Modern Zenhouse Sculptor Studio

studio, Stamford
New Beach Home Near Stamford Downtown/shippan - Stamford, CT
10 25 reviews

New Beach Home Near Stamford Downtown/shippan

apartment, Stamford
One Bedroom With Modern Kitchen, Balcony With Water View - Stamford, CT
8.8 34 reviews

One Bedroom With Modern Kitchen, Balcony With Water View

apartment, Greenwich

Compare Dog-Friendly Self-Catering Rentals in Stamford, CT

These dog-friendly holiday rentals and Airbnbs in Stamford, CT feature outdoor showers and access to pet-welcoming beaches.

Private, Cozy Studio In Downtown Stamford, Ct - Stamford, CT
No reviews

Private, Cozy Studio In Downtown Stamford, Ct

studio, Stamford
Stylish Home With Free Parkingfa - Stamford, CT
No reviews

Stylish Home With Free Parkingfa

apartment, Stamford
A-frame Loft Near Metro-north | Queen + Kitchen - Stamford, CT
10 9 reviews

A-frame Loft Near Metro-north | Queen + Kitchen

apartment, Stamford
Cozy 1bd Studio In Downtown Stamford - Stamford, CT
9.2 19 reviews

Cozy 1bd Studio In Downtown Stamford

apartment, Stamford

Our Favourite Self-Catering Rentals with a Hot Tub in Stamford, CT

A holiday rental or Airbnb with a hot tub near the water in Stamford, CT is ideal for a private evening soak.

Cove Park Sunsets |Hot Tub/fire Pit/bbq/ev Charger - Stamford, CT
10 79 reviews

Cove Park Sunsets |Hot Tub/fire Pit/bbq/ev Charger

apartment, Stamford
Your 5 Star Luxury Countryhome Getaway/w Brand New 7 Seater Hot Tub! - Stamford, CT
9.4 18 reviews

Your 5 Star Luxury Countryhome Getaway/w Brand New 7 Seater Hot Tub!

apartment, Stamford
Ocean Coast Luxury Beach House / Across The Road From The Beach, 45 Min To Nyc - Stamford, CT
9.9 144 reviews

Ocean Coast Luxury Beach House / Across The Road From The Beach, 45 Min To Nyc

apartment, Stamford
Walktowater+pool+fire Pit+grill+game Room - Stamford, CT
10 5 reviews

Walktowater+pool+fire Pit+grill+game Room

apartment, Stamford

Guest-Favourite Holiday Rentals with a Spa in Stamford, CT

Wellness travel to Stamford, CT starts with a holiday rental that features a proper spa.

Hidden Gem| Private Studio In Stamford Dwtn - Stamford, CT
No reviews

Hidden Gem| Private Studio In Stamford Dwtn

apartment, Stamford
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