Best apartment offers in Dutchess County, NY

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Dutchess County, NY apartments
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944 Holiday apartments Dutchess County, NY

Best family friendly Dutchess County, NY Holiday Apartments and Self Catering Accommodations

Among the 944 accommodations in Dutchess County, NY, here are the 4 best family friendly holiday apartments

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat - Dutchess County, NY
10 5 reviews
Dutchess County, NY
23/06 – 04/07
SG$588/nighttotal: SG$6468 (11 )

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

3 2
apartment , Fairview
This Fairview holiday home is situated within 5km of King Street Dog Park, Richard L. Skimin Memorial Baseball Field, Chance Theatre, Mid-Hudson Heritage Center, and Walkway Over the Hudson State Historic Park, offering easy access to local attractions.
This 214 square metre property sleeps six guests, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, a terrace, garden, parking, and a fireplace; ideal for families.
Cleos Cabin: Private Retreat With Fenced Dog Run - Dutchess County, NY
9.0 12 reviews
Dutchess County, NY
23/06 – 04/07
SG$710/nighttotal: SG$7810 (11 )

Cleos Cabin: Private Retreat With Fenced Dog Run

3 2
apartment , Glasco
This Glasco lodge boasts a scenic 2-acre setting near the waterfront, a short drive (approx. 16 km) from Saugerties, and within easy reach of Woodstock and Kingston.
The 149 square metre property offers three bedrooms, two bathrooms, sleeps eight guests, and includes a chef's kitchen, multiple workspaces, a fenced dog run, and a wood-burning stove; nearby activities include skiing at Hunter Mountain (approx. 56 km).
3 Bedrooms Close To Rhinebeck Ny - Dutchess County, NY
9.9 124 reviews
Dutchess County, NY
23/06 – 04/07
SG$380/nighttotal: SG$4180 (11 )

3 Bedrooms Close To Rhinebeck Ny

1 2
apartment , Staatsburg
This apartment is situated in Staatsburg, just 10km from Rhinebeck and Hyde Park, offering easy access to shops, restaurants, and historic sites. It has received excellent ratings for its location, cleanliness, and overall experience.
The three-bedroom property can comfortably accommodate up to four guests. It features a modern kitchen, a spacious living room, and a cosy dining area, as well as a garden, a patio, and a fire pit for outdoor enjoyment.
Steps To The Delightful Village Of Millbrook  Fun Family Getaway - Dutchess County, NY
10 3 reviews
Dutchess County, NY
23/06 – 04/07
SG$657/nighttotal: SG$7227 (11 )

Steps To The Delightful Village Of Millbrook Fun Family Getaway

3 2
apartment , Millbrook
This chic upstate retreat is situated in Millbrook, a village with a single traffic light, offering convenient walking access to local shops, eateries, and parks, and is approximately 14.5 kilometres from the Metro North Rail for journeys to New York City.
This three-bedroom, one-bathroom holiday home accommodates up to eight guests and boasts a modern kitchen with a Wolf gas stove and Nespresso machine, air conditioning, Wi-Fi, a dedicated movie theatre, and family-friendly outdoor activities including a zipline and tree house, with pets welcome.

Top cities

Best Dutchess County, NY apartment rentals with a garden

Livingupstation - Dutchess County, NY
9.7 124 reviews
Dutchess County, NY
23/06 – 04/07
SG$470/nighttotal: SG$5170 (11 )

Livingupstation

1 2
apartment , Brinckerhoff
This three-bedroom, two-bathroom apartment near Brinckerhoff, Upstate New York, is less than 145 kilometres from Grand Central Terminal by train and minutes from Dia Beacon.
The property, boasting a mid-century modern design with a wood-burning fireplace and Finnish sauna, sleeps eight guests and features a sunken living room, garden, and parking; nearby attractions include Dia Beacon and various fine-dining restaurants.
Hidden Gem Cottage —  Cozy Escape To Play Or Wfh - Dutchess County, NY
9.9 248 reviews
Dutchess County, NY
23/06 – 04/07
SG$217/nighttotal: SG$2387 (11 )

Hidden Gem Cottage — Cozy Escape To Play Or Wfh

1 2
apartment , Port Ewen
This brand new Port Ewen cottage, situated near the Hudson River and within a 32km radius of various towns, offers a peaceful retreat in a natural setting.
The self-catering property boasts a 1-bedroom open-plan design sleeping up to four guests, featuring a queen-size bed, pull-out queen sofa bed, 55-inch Apple TV, Wi-Fi, BBQ, firepit, and optional in-house meals/personal training sessions.
Village Retreat  Hot Tub & Views - Dutchess County, NY
10 1 review
Dutchess County, NY
23/06 – 04/07
SG$505/nighttotal: SG$5555 (11 )

Village Retreat Hot Tub & Views

1 2
apartment , Saugerties
This Saugerties flat is situated within a short walk to Esopus Creek and the Saugerties Village waterfront, offering convenient access to local attractions such as the Kiwanis Ice Arena and Hudson Maritime Museum, with natural sites like Kaaterskill Falls and Esopus Bend Nature Preserve also nearby.
This property accommodates up to four guests in two bedrooms and two bathrooms, featuring a full kitchen with an oven and microwave, air conditioning, Wi-Fi, a barbecue, and a garden with a balcony for outdoor relaxation.
Grand Arcady - 3br/2ba Renovated Farm House - Dutchess County, NY
9.6 119 reviews
Dutchess County, NY
23/06 – 04/07
SG$448/nighttotal: SG$4928 (11 )

Grand Arcady - 3br/2ba Renovated Farm House

3 2
apartment , Salt Point
This charming 1860s farmhouse is situated in Salt Point, just a short drive from Rhinebeck, Millbrook, and the Omega Institute, offering easy access to the Hudson Valley's attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers a spacious three-bedroom apartment, comfortably accommodating up to seven guests. This charming retreat offers a private creek, vineyard, shared fire pit, screened-in porch, and a nearby town beach for swimming and other water activities.

Frequently asked questions about apartment rentals in Dutchess County, NY

  • What is Dutchess County, New York, famous for?

    Dutchess County is renowned for its stunning landscapes, blending rolling hills, the Hudson River, and charming towns. It's a popular destination for its historical sites like the Vanderbilt Mansion National Historic Site and the Home of Franklin D. Roosevelt National Historic Site, offering a glimpse into American history. The county also boasts a thriving arts and culture scene, with numerous galleries, theatres, and festivals throughout the year. Additionally, its agricultural heritage is significant, with many farms and farm-to-table restaurants showcasing the region's produce.
  • What are the best apartments in Dutchess County, NY?

  • What are some off-the-beaten-path spots to check out in Dutchess County, New York?

    For a less-travelled experience, explore the Walkway Over the Hudson State Historic Park for breathtaking river views. Consider a visit to the quirky Dia Beacon, a contemporary art museum housed in a former Nabisco box printing factory. The charming village of Tivoli, with its unique shops and restaurants, is another hidden gem. For nature lovers, the extensive trail system at the Stissing Mountain State Forest offers opportunities for hiking and enjoying the natural beauty of the county.
  • What are the best apartments with a pool in Dutchess County, NY?

  • When should one visit Dutchess County, New York, for the best experience?

    The best time to visit Dutchess County depends on your preferences. Spring and autumn offer pleasant temperatures and vibrant foliage, ideal for hiking and exploring the outdoors. Summer is warm and perfect for water activities on the Hudson River, but it can get crowded. Winter brings a quieter atmosphere, with opportunities for skiing and snowboarding at nearby resorts, and a charming festive ambiance in the towns.
  • What are the best apartments with a jacuzzi in Dutchess County, NY?

  • Are there any cultural festivals unique to Dutchess County, New York?

    Dutchess County hosts various events throughout the year. The annual Dutchess County Fair is a large-scale event showcasing local agriculture and entertainment. Many towns and villages also host smaller, community-based festivals celebrating local arts, crafts, and food. Check local listings for specific dates and events.
  • What are the best apartments for families and kids in Dutchess County, NY?

  • What sports or recreational activities are a big draw in Dutchess County, New York?

    Hiking and biking are very popular, with numerous trails throughout the county. The Hudson River offers opportunities for kayaking, canoeing, and fishing. Nearby ski resorts provide winter sports options. Golfing is another popular activity, with several courses in the area. For a more relaxed activity, explore the many farm stands and pick-your-own farms.
  • What are the best pet friendly apartments in Dutchess County, NY?

  • How can one best interact with locals to learn about Dutchess County, New York's traditions?

    Visiting local farmers' markets is a great way to meet residents and learn about the area's agricultural heritage. Striking up conversations with staff at local businesses, such as antique shops or restaurants, can also provide insights into the community's history and culture. Attending local events and festivals offers further opportunities for interaction and cultural immersion.
  • What are the best apartments with parking in Dutchess County, NY?

  • What are the best local dishes to try in Dutchess County, New York?

    Dutchess County's culinary scene is influenced by its agricultural bounty. Look for dishes featuring locally sourced ingredients, such as fresh produce, dairy products, and meats. Many restaurants offer farm-to-table menus highlighting seasonal specialties. Apple picking is a popular autumn activity, and local cideries offer delicious apple cider and other treats.
  • What specific items should one pack for a trip to Dutchess County, New York?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Layers of clothing are recommended, as the weather can change unexpectedly. If you plan on hiking, bring appropriate outdoor gear. Don't forget sunscreen, insect repellent, and a reusable water bottle to stay hydrated.
  • What are the top sights to visit in Dutchess County, New York?

    The Vanderbilt Mansion National Historic Site and the Home of Franklin D. Roosevelt National Historic Site are must-sees for history buffs. The Walkway Over the Hudson State Historic Park provides spectacular views. Dia Beacon offers a unique art experience. For a charming small-town experience, explore Beacon and Cold Spring. Numerous hiking trails and farms offer opportunities to explore the county's natural beauty.

Nearby regions

Best Dutchess County, NY holiday apartments with a kitchen

2 Full Beds | Non-smoking, Kitchen - Dutchess County, NY
9.2 16 reviews
Dutchess County, NY
23/06 – 04/07
SG$189/nighttotal: SG$2079 (11 )

2 Full Beds | Non-smoking, Kitchen

1 2
apartment , Fishkill
This apartment in Fishkill is situated 10.9 kilometres from the Mid Hudson Children's Museum and 19.3 kilometres from Stewart International Airport.
This 33 square metre flat offers one bedroom and one bathroom, accommodating up to four guests, with a kitchen equipped with a fridge and microwave oven, air conditioning, and complimentary WiFi.
Stone Carriage House -Bring Your Dogs! - Dutchess County, NY
9.8 23 reviews
Dutchess County, NY
23/06 – 04/07
SG$340/nighttotal: SG$3740 (11 )

Stone Carriage House -Bring Your Dogs!

1 2
apartment , Port Ewen
This stone carriage house, situated in Union Center, Ulster Park, New York, is a short drive from Kingston and offers easy access to the Ashokan Reservoir and Rondout Creek.
The self-catering cottage sleeps two guests in one bedroom and one bathroom, boasting a fully equipped kitchen, wood-burning stove, and picnic basket for enjoying the three-acre grounds, which include various seating areas and proximity to the Headless Horseman Hayrides (seasonal).
The Bennett Cabin - Dutchess County, NY
9.7 109 reviews
Dutchess County, NY
23/06 – 04/07
SG$268/nighttotal: SG$2948 (11 )

The Bennett Cabin

1 2
apartment , Millbrook
This Millbrook duplex apartment is situated on a five-acre estate bordering a creek, within walking distance of Orvis Sandanona, 3.2km from Millbrook Village, and 4.8km from Millbrook Vineyards, offering easy access to local amenities and Hudson Valley historical sites.
The self-contained flat comprises one bedroom, one bathroom, and can accommodate two guests, featuring a kitchen with fridge, freezer and microwave, air conditioning, parking, a garden, and excellent guest reviews; enjoy the tranquil creekside setting.
Historic 1 Br Family Home Near Buttermilk Falls - Dutchess County, NY
9.5 191 reviews
Dutchess County, NY
23/06 – 04/07
SG$299/nighttotal: SG$3289 (11 )

Historic 1 Br Family Home Near Buttermilk Falls

1 2
apartment , Milton
This charming 1790 Stagecoach Stop is situated in Milton, New York, directly across the street from Buttermilk Falls Resort & Spa and just a short drive from Walkway Over The Hudson. The property has received excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom, one-bathroom cottage can comfortably accommodate up to four guests and features a spacious kitchen, living room, and a sunroom with stunning views. Guests can enjoy a private garden, a fire pit, and modern conveniences like air conditioning, a coded deadbolt, and Roku Guest Mode for streaming entertainment.

Best Dutchess County, NY holiday apartments with air conditioning

Trailside Base W/ Gazebo & Kayaks - Dutchess County, NY
Dutchess County, NY
23/06 – 04/07
SG$284/nighttotal: SG$3124 (11 )

Trailside Base W/ Gazebo & Kayaks

2 2
apartment , Lake Carmel
This ground-level flat in Stormville offers direct access to the Appalachian Trail, just 2 kilometres from Lake Carmel, with a private gazebo featuring a gas grill and a large garden with a fire pit.
Accommodating up to four guests, this two-bedroom apartment provides a fully equipped kitchen, air conditioning, and complimentary kayaks for exploring nearby waters, with shared driveway parking for three vehicles.
Casa Fuego Catskills - Historic Fire House - Dutchess County, NY
10 54 reviews
Dutchess County, NY
23/06 – 04/07
SG$355/nighttotal: SG$3905 (11 )

Casa Fuego Catskills - Historic Fire House

2 2
apartment , Saugerties
This historic firehouse, located a short walk from Saugerties' Main Street restaurants and less than 10 minutes from Village Beach, offers a unique and charming stay in the heart of this vibrant village. The accommodation has received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The renovated firehouse features a spacious open floor plan, accommodating up to four guests. The property offers a range of amenities, including a fully equipped kitchen with modern appliances, a heated toilet and bidet, and a Level 2 electric car outlet, making it a convenient choice for travellers.
Your Own Pied-a-terre "Walkway Over The Hudson" #3 - Dutchess County, NY
9.9 81 reviews
Dutchess County, NY
23/06 – 04/07
SG$175/nighttotal: SG$1925 (11 )

Your Own Pied-a-terre "Walkway Over The Hudson" #3

1 2
apartment , Poughkeepsie
This studio apartment is conveniently located in Poughkeepsie, within easy walking distance of the Dutchess County Courthouse, Marist and Vassar Colleges, Vassar Brothers Medical Center, the Walkway Over the Hudson, the train station, and Hudson River Park. The property has received excellent ratings for cleanliness, location, and overall guest experience.
The self-contained apartment has a private entrance and can comfortably accommodate two guests. Enjoy the convenience of a fully equipped kitchen, a private garden, complimentary bicycles, and access to a gas and charcoal grill, a fire pit, and a patio.
Spacious Studio In Hudson Valley - Dutchess County, NY
9.6 323 reviews
Dutchess County, NY
23/06 – 04/07
SG$176/nighttotal: SG$1936 (11 )

Spacious Studio In Hudson Valley

1 2
apartment , Nelsonville
This studio apartment is situated in a converted barn in Cold Spring, a historic town in the Hudson Valley, just 8 kilometres from Nelsonville. The property has received excellent ratings for its cleanliness, location, and overall experience.
The studio comfortably sleeps four guests in a queen-size bed and a queen-size pull-out sofa bed. The kitchen is equipped with a fridge, microwave, toaster oven, coffee maker, and electric kettle, allowing guests to prepare simple meals and snacks.
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