The Hill holiday lettings

We found 108 holiday rentals — enter your dates for availability

Discover a selection of 17 apartments and other holiday rentals in The Hill that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the amenities that you expect and more, including Wi-Fi and parking. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

Why visit The Hill

  • Outdoor Activities: The Hill boasts beautiful beaches and state parks, perfect for nature enthusiasts and family outings.
  • Cultural Attractions: Discover local heritage at the Hill Museum and participate in the vibrant Hill Festival.
  • Charming Neighbourhood: Experience the warm community spirit of the upper Hill neighbourhood, filled with friendly locals.
  • Diverse Accommodation: Choose from a variety of lodging options, including cosy cottages and modern apartments, to suit your needs.
  • Proximity to Downtown: Enjoy easy access to downtown New Haven, offering excursions and activities for all budgets.

Popular types of accommodation around The Hill

You've chosen The Hill for your getaway, and now it’s time to find the perfect place to stay. From charming houses and cosy cottages to modern apartments, The Hill offers a variety of accommodation options. Consider individual apartments in vibrant Chapel Street or spacious homes in New Haven and Newhallville, ensuring you have a comfortable base to explore all that this delightful area has to offer.

  • Houses: The top choice for accommodation in The Hill, offering spacious and comfortable settings ideal for families and groups.
  • Cottages: A charming option for those seeking a quaint and cosy retreat in the area.
  • Apartments: Perfect for couples or solo travellers, providing a convenient and self-catering experience.
  • Condos: A popular choice for those who prefer modern amenities in a communal setting.
  • Villas: Luxurious and often spacious, villas are an excellent option for a more upscale stay.**

Top attractions near The Hill

The Hill in New Haven, Connecticut, is perfect for outdoor and cultural family holidays. Visitors can explore local attractions such as beautiful beaches, historic colleges, and state parks. Notable points of interest include the Hill Museum, Sodom Hill, and the Hill Festival, offering a delightful mix of activities for all ages. Whether you're seeking adventure or cultural experiences, The Hill has something to offer every traveller.

  • Yale University: A prestigious institution steeped in history and tradition, featuring stunning architecture and beautiful campus grounds. Visitors can explore its rich cultural atmosphere, making it a vibrant place for learning and discovery.
  • Yale University Art Gallery: An exceptional art museum showcasing an impressive collection of artworks from various periods and cultures. The gallery provides a unique cultural experience, perfect for art enthusiasts and casual visitors alike.
  • Yale Bowl: A historic sports stadium known for its distinctive architecture and significant role in American football. With a lively atmosphere during games, it offers a blend of sports excitement and cultural heritage.

Things to do recommended for couples

If you're seeking a romantic getaway, start with a concert at Woolsey Hall, a mere mile from The Hill. For adventure lovers, Waterski Connecticut offers thrilling water sports, only 6.2km away. Finally, indulge in romance at Gouveia Winery, situated 8.1km away, perfect for a delightful wine tasting experience.

Things to do recommended for families

Families visiting The Hill in New Haven can enjoy an active day at the Connecticut Sportsplex, unwind at the serene East Rock Park, or engage in fitness activities at the Payne Whitney Gymnasium, all offering fantastic experiences suitable for children and parents alike.

Things to do recommended for groups

Enjoy a night out at the Shubert Theatre for a cultural experience, indulge in some retail therapy at Westfield Connecticut Post Mall, or challenge your mates to a round of golf at the scenic Yale Golf Course. Each offers a unique vibe for your group adventure!

What do I need to keep in mind when booking a vacation around The Hill

Regardless of whether you're travelling with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, it's important to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to The Hill with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas suitable for group gatherings. Thankfully, you can easily narrow down your options on Vrbo to include all these preferences and more.
  • Traveling to The Hill with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to The Hill: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting The Hill: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near The Hill

The Hill in New Haven, Connecticut, offers a delightful blend of outdoor activities and cultural experiences, perfect for family-friendly vacations. Explore the charming upper Hill neighbourhood, where friendly locals and vibrant community spirit abound. Just a short journey to downtown, you’ll find excursions that cater to all budgets, making it an ideal base for discovering the rich atmosphere of New Haven and its surrounding areas.

  • New Haven: Situated merely 621m from The Hill, New Haven is a vibrant city steeped in culture and history. Known for its prestigious educational institutions, including the renowned Yale University, the city offers a wealth of cultural experiences. Explore the local shopping areas or catch a live music concert at one of the many venues. New Haven also boasts picturesque beaches and historic landmarks, making it a perfect destination for families and culture enthusiasts alike.
  • Milford: Located 5.0km from The Hill, Milford is a charming city that invites visitors to indulge in outdoor activities and family-friendly experiences. The city is known for its beautiful recreational areas and golf courses, providing ample opportunities for relaxation and leisure. Milford’s beaches are perfect for a family day out, where you can enjoy sunbathing or a seaside picnic. Additionally, the presence of historic educational institutions adds to the city’s allure.
  • West Haven: Just 1.2km from The Hill, West Haven is a delightful city that combines cultural experiences with outdoor fun. Its proximity to the beach and recreational areas makes it an ideal spot for families looking to enjoy nature. The city features a variety of shopping areas and educational venues, catering to diverse interests. Families will particularly appreciate the welcoming atmosphere and the array of activities available for all ages.

Best time to go to The Hill

If you're planning a trip to The Hill, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnyLowSlightly Low
February32.4°F (0.2°C)Light RainMostly SunnyLowSlightly Low
March38.5°F (3.6°C)Light RainMostly SunnyLowSlightly Low
April48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
May58.3°F (14.6°C)Light RainMostly SunnyAverageAverage
June66.9°F (19.4°C)Light RainMostly SunnyHighSlightly High
July74.1°F (23.4°C)Light RainMostly SunnyHighSlightly High
August73.2°F (22.9°C)Light RainMostly SunnyHighSlightly High
September66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November45.5°F (7.5°C)Light RainMostly SunnyAverageAverage
December37.8°F (3.2°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as this can lead to significant savings due to fluctuating prices. Furthermore, opting for a longer stay often results in even better deals. To discover the ideal Vrbo accommodation that fits your budget, make use of our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new holidays, resume your previous arrangements, or review and organise your travel itineraries. You'll discover your saved or booked properties neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in The Hill?
In The Hill, apartments are the most popular type of holiday rental, with around 13 available in the area. These apartments are often located in peaceful neighbourhoods, providing a comfortable and homely atmosphere. Travellers can expect amenities such as fully equipped kitchens, cosy living areas, and sometimes private balconies for enjoying the serene surroundings.
Are there any beach house rentals in The Hill?
In The Hill, Connecticut, beach house rentals are available, appealing to those seeking a coastal getaway. These properties are typically situated in scenic locations near the shoreline, providing easy access to local beaches and waterfront activities. Amenities commonly found in these rentals include spacious living areas, fully equipped kitchens, and outdoor decks or patios for enjoying the fresh sea breeze. Many homes also feature multiple bedrooms, making them suitable for families or groups looking to share a memorable holiday experience.
How much does it cost to rent a holiday home in The Hill?
Prices for holiday rentals in The Hill 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in The Hill to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for The Hill holiday house rentals?
You can find great discounts on house rentals in The Hill on Vrbo, 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.
Are there any The Hill holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in The Hill 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 on Vrbo 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.
Can I find long-stay holiday rentals in The Hill?
A long-stay holiday rental in The Hill 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit The Hill for a holiday rental?
September is the most popular time to visit The Hill, as the summer heat begins to ease and the landscape dons its autumn colours. This month marks the transition into a beautiful fall season, making it ideal for outdoor enthusiasts who enjoy hiking and exploring the area's scenic parks. The peak season runs from July to September, during which visitors can partake in various activities, including local festivals and outdoor concerts, all while enjoying mild temperatures around the low 20s Celsius.

For those considering a more budget-friendly option, May serves as a fantastic time to visit The Hill. This month often sees fewer crowds, allowing for a more peaceful experience while still enjoying the lush greenery and blooming flowers that create a picturesque setting. You'll have the opportunity to explore local attractions without the hustle and bustle of the peak tourist season.
Are there any remote work holiday rentals in The Hill?
In The Hill, Connecticut, there are about 10 remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties offer essential amenities for remote work, including Wi-Fi, dedicated desk spaces, and comfortable chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a The Hill holiday rental?
Book your The Hill holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my The Hill home rental booking on Vrbo?
To find The Hill holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the The Hill holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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