Stratford holiday rentals

We found 590 holiday rentals — enter your dates for availability
Discover a selection of 14 homes and other holiday rentals in Stratford that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Stratford

Showing deals for:18 Dec - 25 Dec

Sunsets are simply breath taking over the water
You will love the Center Island cooktop open kitchen & beautiful water views
3rd Guest Bedroom - Queen Size - Harbor Views
Cozy seating area with dual water views
Exceptional
(74 reviews)

Waterfront Retreat, Private Beach + Hot Tub Sunsets

Branford

15% off
AU$14,829
for 7 nights, 1 home
AU$2,118 per night
includes taxes & fees
Waterfront Retreat, Private Beach + Hot Tub Sunsets
Kitchen
View of back of house
Stairs leading to third floor
Front of house
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
AU$12,290
for 7 nights, 1 home
AU$1,756 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Pool
Living area
Living area
Terrace/patio
Exceptional
(5 reviews)

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

Fairfield

8% off
AU$30,062
for 7 nights, 1 home
AU$4,295 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Open layout living
Enjoy lounging after a long beach day on the sectional looking out at the water
Fully stocked kitchen with stainless steel appliances and breakfast counter
Exterior
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

8% off
AU$9,052
for 7 nights, 1 home
AU$1,293 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Property grounds
Living area
Living area
Private kitchen
Exceptional
(11 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
AU$3,959
for 7 nights, 1 cottage
AU$566 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Home from the water. (Blue house in center of photo)
Interior
Living area
master bedroom, king bed.
Exceptional
(54 reviews)

Beautiful Waterfront Beach House for Family Vacations

Branford

8% off
AU$8,555
for 7 nights, 1 home
AU$1,222 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Living area
Outdoor dining
Living area
Kitchen
Exceptional
(8 reviews)

Silver Sands Beach Getaway

Milford

16% off
AU$4,359
for 7 nights, 1 home
AU$623 per night
includes taxes & fees
Silver Sands Beach Getaway
Living room, bathed in morning light
Back deck
Kitchen
Interior
Wonderful
(90 reviews)

Historic New England home ,Reunions Beach pass

Guilford

8% off
AU$5,685
for 7 nights, 1 home
AU$812 per night
includes taxes & fees
Historic New England home ,Reunions Beach pass
Dining Room
Stairwell to Master
Living Room
Queen Bedroom 2
Excellent
(6 reviews)

Beach Apartment in Woodmont Milford

Milford

8% off
AU$3,101
for 7 nights, 1 apartment
AU$443 per night
includes taxes & fees
Beach Apartment in Woodmont Milford

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Delight in the beachside landscape of Stratford

Enjoy the entertainment and other features of Stratford. This city's baseball games, beaches and cycling draw many visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Stratford

Do you want to find attractions to see in the area? Venture out of your cosy holiday rental and experience everything that Stratford has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Beardsley Zoo (3.1 mi / 5 km)
  • Norwalk Maritime Aquarium (15.9 mi / 25.5 km)
  • Great River Golf Club (6.8 mi / 10.9 km)
  • Country Club of Fairfield (8.3 mi / 13.4 km)
  • Connecticut Golf Club (11.7 mi / 18.8 km)
  • Yale Golf Course (12 mi / 19.4 km)

Exploring the natural landscape of Stratford

Whether you're an outdoor enthusiast or just want to take in the scenery, Stratford is a great place to get outside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Short Beach (1.8 mi / 2.9 km)
  • Lordship Beach (2.6 mi / 4.2 km)
  • Walnut Beach (3 mi / 4.8 km)
  • Silver Sands (3.6 mi / 5.9 km)
  • Seaside Park (3.7 mi / 5.9 km)
  • Seaside Beach (4 mi / 6.4 km)

Seasonal weather averages in Stratford

If you're hoping to enjoy some warm-weather activities on your holiday, July, August, June and September are the hottest months to visit, when temperatures average 22°C.

How to get to and around Stratford

The nearest airport is in Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), located 1.6 mi (2.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is 13.9 mi (22.3 km) away.

Frequently asked questions

What is the best area to stay in Stratford when booking a holiday rental?
When considering a holiday rental in Stratford, Connecticut, one of the best areas to explore is the picturesque neighbourhood near Long Beach. This area is renowned for its beautiful sandy shores and tranquil waterfront, making it an ideal spot for families or anyone seeking relaxation by the sea. The nearby Long Beach Park offers lovely walking paths and picnic areas, superb for enjoying a sunny day outdoors.Another appealing option is the historic downtown Stratford area, which features charming architecture and a vibrant setting. Here, visitors can enjoy a range of local shops, cafes, and restaurants, providing a delightful taste of the community. The nearby Shakespeare Theatre is a cultural highlight, attracting theatre enthusiasts and offering a variety of performances throughout the year.In terms of accommodation, Stratford boasts a diverse selection of properties, suiting different preferences and budgets. Whether you're looking for a cosy cottage or a modern apartment, you can find something to suit your needs in these inviting neighbourhoods.
Where are the best areas for renting a beach house in Stratford?
For renting a beach house in Stratford, the best areas are along the picturesque coastline near Long Beach and the scenic shores of the Housatonic River. Long Beach is particularly popular, offering a range of holiday rentals just steps from the sandy shore and the inviting waters, making it ideal for families looking to enjoy a traditional beach experience. Many properties in this area come with amenities such as private decks, outdoor dining spaces, and barbecue grills, superb for summer gatherings.In addition, the area around the Stratford Point Light provides a more tranquil setting, where visitors can find charming cottages with stunning views of the lighthouse and the Long Island Sound. These rentals often feature amenities like fully equipped kitchens, spacious living areas, and sometimes even private access to the beach.Furthermore, the nearby Short Beach area presents additional options, where holiday homes amidst lush greenery can be found, often equipped with modern comforts such as Wi-Fi, air conditioning, and laundry facilities. This location is ideal for those looking to enjoy both beach activities and the natural beauty of local parks, with easy access to scenic walking paths and picnic spots along the coast.
What is the most popular type of holiday rental accomodation in Stratford?
In Stratford, holiday houses are the most popular type of holiday rental, with around 36 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, ideal for families or groups looking for comfort and convenience. Many also include outdoor spaces such as gardens or patios, great for relaxing after a day of exploring local attractions like the Stratford Historical Society or the scenic waterfront. Additionally, there are about 12 apartments and several cottages, providing a variety of options to suit different preferences and group sizes.
Are there any family house rentals in Stratford?
In Stratford, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The neighbourhoods around the town centre and near the waterfront provide a variety of options to suit different needs. Many properties feature spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces where children can play freely.Visitors can also find homes equipped with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay. Close by, families can explore local parks and the scenic shoreline, which offer recreational opportunities and a chance to enjoy the outdoors.
Can I rent a holiday home with a pool or hot tub in Stratford?
In Stratford, Connecticut, there are several holiday homes available for rent that feature pools or hot tubs, making it a great option for those seeking relaxation. The town is known for its beautiful coastal setting and offers a variety of neighbourhoods where these properties can be found, including the scenic waterfront areas and quieter residential districts.Travellers can expect amenities such as private swimming pools, inviting hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens, ideal for family gatherings or entertaining guests. Some rentals may also offer additional comforts like barbecue facilities and easy access to local parks or beaches, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Stratford?
In Stratford, there are several pet-friendly house rentals available, making it an excellent choice for travellers with furry companions. The area offers a variety of holiday rentals, often featuring amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ideal for families or groups. Many properties are conveniently located near parks, providing ample space for pets to play and enjoy the outdoors.Additionally, the proximity to Long Beach offers a lovely spot for walks along the shoreline, where you and your pet can enjoy the fresh air and scenic views. The local community also has several pet-friendly cafes and shops, ideal for those travelling with pets.
Are there any remote work holiday rentals in Stratford?
In Stratford, Connecticut, there are numerous remote work-friendly holiday rentals available, with around 45 options to choose from. Many of these properties are equipped with amenities that cater specifically to those working remotely, including free Wi-Fi both in rooms and public areas, as well as designated desks within the accommodations. This makes it easy for travellers to maintain productivity while enjoying their stay.The town itself is charming, with easy access to local parks and waterfront areas for relaxation after a day of work. Stratford's proximity to the bustling city of Bridgeport also offers additional dining and entertainment options, enhancing the overall experience for those combining work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Stratford?
In Stratford, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and desks equipped with chairs, ideal for those needing to work or study during their stay. Onsite parking is also a common feature, providing convenience for travellers with cars. Additionally, many rentals come with coffee and tea makers, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit Stratford for a holiday rental?
The peak season for holiday rentals in Stratford is from May to July, with July being the most popular month. This vibrant period attracts visitors eager to enjoy the warm weather, local festivals, and the beautiful coastal scenery. With temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for outdoor activities like strolling along the waterfront or exploring the charming parks and gardens.During these months, the town buzzes with life as tourists flock to enjoy the local attractions, including the famed Stratford Festival, which showcases outstanding performances and draws theatre enthusiasts from near and far. The lively option is superb for those looking to immerse themselves in culture while enjoying the convenience of nearby dining and entertainment options.For travellers seeking a more budget-friendly experience, consider visiting in December. While it's the low season, this month offers a unique charm, with festive decorations and a quieter atmosphere ideal for those who appreciate a more relaxed experience. You can explore the town's winter beauty while enjoying the local holiday spirit.Ultimately, your choice of when to visit Stratford should reflect your personal preferences—whether you're drawn to the bustling summer activities or the serene beauty of winter.
What are the top attractions in Stratford?
In Stratford, Connecticut, visitors can explore a variety of attractions that highlight the area's rich history and natural beauty. The Shakespeare Festival Theatre is a prominent cultural venue, offering performances and events that celebrate the works of the iconic playwright. Nearby, the Stratford Historical Society provides insights into the town's past, with exhibits and programmes that delve into local history.For those who enjoy the outdoors, the scenic Long Beach offers a beautiful shoreline ideal for sunbathing and leisurely strolls, while the nearby Stratford Point provides stunning views of the Long Island Sound and is a great spot for birdwatching. The area's parks, such as Roosevelt Forest, feature walking trails and picnic areas, making them superb for family outings.Additionally, the charming downtown area features shops and eateries, allowing visitors to experience the local flavour and community spirit.
Are all fees included in the Stratford holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Stratford holiday homes with parking?
Stayz offers a wide selection of holiday homes in Stratford with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Stratford holiday homes?
You can find great discounts on holiday homes in Stratford on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Stratford holiday home booking on Stayz?
To find Stratford holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Stratford?
A long-stay holiday home in Stratford is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Stratford holiday home?
Book your Stratford holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Stratford?
Prices for holiday homes in Stratford vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Stratford to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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