Dover Plains holiday lettings

We found 85 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Dover Plains that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Find the perfect holiday rental for your Dover Plains getaway

Learn about the unique charm of Dover Plains with a stay in a holiday home rental. This city has something for everyone. 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.

Sightseeing in and around Dover Plains

Do you want to discover things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Dover Plains a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Millbrook Vineyards and Winery (8.9 mi / 14.4 km)
  • Hopkins Vineyard (11.7 mi / 18.9 km)
  • Mohawk Mountain Ski Area (15.2 mi / 24.4 km)
  • Thunder Ridge Ski Resort (16.1 mi / 25.9 km)
  • Trevor Zoo (8.2 mi / 13.2 km)
  • McCann Ice Arena (18.4 mi / 29.6 km)

Exploring the natural landscape of Dover Plains

Whether you're an outdoor enthusiast or just want to take in the scenery, Dover Plains is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Kent Falls State Park (8.5 mi / 13.7 km)
  • Lake Waramaug State Park (10.2 mi / 16.4 km)
  • Lake Waramaug (11.5 mi / 18.5 km)
  • Mohawk Mountain State Forest (15.5 mi / 24.9 km)
  • Candlewood Lake (18.2 mi / 29.4 km)
  • Walkway Over the Hudson State Historic Park (19.4 mi / 31.2 km)

Travelling to and around Dover Plains

The nearest airport is in Danbury, CT (DXR-Danbury Municipal), located 25.9 mi (41.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Oxford, CT (OXC-Waterbury - Oxford), which is 29 mi (46.7 km) away.

Frequently asked questions

What is the best area to stay in Dover Plains when booking a holiday rental?
When looking for a holiday rental in Dover Plains, New York, the area around the town centre is an excellent choice. This charming neighbourhood offers a convenient base for exploring the local attractions while providing a taste of the community's welcoming atmosphere. Nearby, you'll find the beautiful Dover Stone Church, a stunning natural rock formation that is great for a picturesque hike or a leisurely stroll. Additionally, the quaint shops and eateries in the vicinity provide a delightful range of dining options and local goods to enjoy.
How much does it cost to rent a holiday home in Dover Plains?
Prices for holiday rentals in Dover Plains 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 Dover Plains 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 Dover Plains holiday house rentals?
You can find great discounts on house rentals in Dover Plains 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.
Where are the best Dover Plains ski resort rentals?
For those seeking ski resort rentals near Dover Plains, the closest ski areas are located in the nearby Catskills region, particularly around the towns of Windham and Hunter. These towns offer a variety of holiday rentals that cater to winter sports enthusiasts looking for convenient access to the slopes. In Windham, you'll find a range of properties, from cozy chalets to spacious cabins, many of which come with amenities such as fireplaces, full kitchens, and sometimes even hot tubs for après-ski relaxation.

In Hunter, the options are similarly appealing, with accommodations located within easy reach of the ski lifts. Many rentals here feature comfortable living areas, ski storage facilities, and outdoor spaces, great for unwinding after a day on the mountain. Both towns also provide access to local shops and restaurants, enhancing the overall experience for travellers.
What is the most popular type of holiday rental accomodation in Dover Plains?
In Dover Plains, various types of holiday rentals are available, with holiday houses being particularly popular—several can be found throughout the area. These homes typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also feature outdoor spaces such as patios or gardens, great for enjoying the serene surroundings. Additionally, there are several campsites and cabins, providing a more rustic experience for those looking to immerse themselves in nature. Apartments are also available, offering a convenient option for couples or solo travellers seeking a comfortable stay.
Are there any family house rentals in Dover Plains?
In Dover Plains, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features spacious homes that often include amenities such as fully equipped kitchens, comfortable living rooms, and outdoor spaces for kids to play. Many properties are conveniently located near local parks and recreational areas, providing opportunities for outdoor activities.
Can I rent a holiday home with a pool or hot tub in Dover Plains?
In Dover Plains, there are several holiday homes available for rent that feature pools and hot tubs, providing travellers with a chance to enjoy a refreshing dip or relax in a warm soak. The area offers a tranquil setting, great for those looking to escape the hustle and bustle. Many of these rentals come equipped with amenities such as spacious outdoor areas, fully equipped kitchens for self-catering, and comfortable living spaces.
Can I find long-stay holiday rentals in Dover Plains?
A long-stay holiday rental in Dover Plains 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.
Are there pet-friendly house rentals in Dover Plains?
In Dover Plains, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. The area features charming properties that often come equipped with amenities such as spacious yards, modern kitchens, and comfortable living spaces, ensuring a pleasant stay for both humans and pets.
Are there any remote work holiday rentals in Dover Plains?
In Dover Plains, New York, there are several remote work holiday rentals available, making it a great choice for those looking to combine work and leisure. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated workspaces, and comfortable desk chairs, ensuring that you can maintain productivity while enjoying a relaxing stay. Additionally, features like safes are often included, providing peace of mind for your belongings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Dover Plains holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Dover Plains 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.
What are popular rental amenities in Dover Plains?
In Dover Plains, popular rental amenities include free in-room Wi-Fi, which is essential for staying connected during your visit. Many properties also feature private pools, allowing guests to enjoy a refreshing swim in the comfort of their own accommodation. Additionally, rentals often come equipped with kitchens, complete with cookware, dishware, and utensils, making it convenient for travellers to prepare their meals.
How early should I book a Dover Plains holiday rental?
Book your Dover Plains 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 Dover Plains home rental booking on Vrbo?
To find Dover Plains 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 Dover Plains 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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