Vacation rentals in New Windsor

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Top-rated vacation rentals in New Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Apartment in Beacon
Sunny 1 Bedroom
Super sunny newly renovated 1BR apartment near Main St in Beacon. Available for stays of 30 night or longer 1 bedroom apartment with a large eat-in kitchen, comfortable living room and sunny workspace. Brand new AC and dishwasher. There is a front porch and a small back yard shared with one other apartment The house is a 6 minute walk to Main St and a 16 minute walk to Mt Beacon. Easy access to tons of fresh air and exercise. Ideal for working from home, moving to the area, visiting family.
Mar 21 – 28
$109 per night
4.93 out of 5 average rating, 137 reviews
Guest favorite
Guest suite in Montgomery
Garden View Guest Cottage
Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people
Aug 23 – 30
$113 per night
4.95 out of 5 average rating, 415 reviews
Guest favorite
Apartment in New Paltz
Modena Mad House
Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in
Jan 28 – Feb 4
$88 per night
4.96 out of 5 average rating, 340 reviews

Popular amenities for New Windsor vacation rentals

Stay near New Windsor's top sights

Destinta Theaters5 locals recommend
Nature's Pantry25 locals recommend
Plum Point Park8 locals recommend
Cilantro Restaurant And Bar4 locals recommend
United States Postal Service3 locals recommend
Kowawese Unique Area3 locals recommend

Other great vacation rentals in New Windsor

Guest favorite
Home in New Windsor
View House
Jul 22 – 29
$247 per night
4.89 out of 5 average rating, 103 reviews
Guest favorite
Tiny home in Newburgh
Cabin in the heart of the Hudson Valley, Cabin 2
Apr 28 – May 5
$112 per night
4.88 out of 5 average rating, 508 reviews
Guest favorite
Apartment in Newburgh
Eco MidCentury Modern Retreat
Jul 27 – Aug 3
$115 per night
4.93 out of 5 average rating, 211 reviews
Guest favorite
Guest suite in Newburgh
Salvick House, Central to all Bethels
Dec 28 – Jan 4
$148 per night
4.99 out of 5 average rating, 150 reviews
Guest favorite
Guest suite in Chester
Adorable Guest Apartment in Victorian Mansion
Sep 21 – 28
$92 per night
4.95 out of 5 average rating, 222 reviews
Guest favorite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
Jan 30 – Feb 6
$110 per night
4.94 out of 5 average rating, 185 reviews
Guest favorite
Guesthouse in Peekskill
Peekskill Carriage House Downtown Studio
Jul 11 – 18
$117 per night
4.94 out of 5 average rating, 203 reviews
Guest favorite
Cottage in Newburgh
Cozy Lake Cottage
May 7 – 14
$100 per night
4.88 out of 5 average rating, 184 reviews
Guest favorite
Home in New Windsor
Cozy cottage with hot tub and game room
Sep 2 – 9
$246 per night
5.0 out of 5 average rating, 43 reviews
Guest favorite
Apartment in New Windsor
Cozy 2 br in-law apt, prime Hudson Valley location
Jul 6 – 13
$150 per night
4.82 out of 5 average rating, 91 reviews
Guest favorite
Home in New Windsor
4 Bd Paradise- Gorgeous Design Close to All!
Feb 7 – 14
$194 per night
4.98 out of 5 average rating, 46 reviews
Guest favorite
Home in Newburgh
Lovely home in town of Newburgh
Jun 10 – 17
$146 per night
4.97 out of 5 average rating, 38 reviews

Quick stats about vacation rentals in New Windsor

Total rentals

30 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

2.3K reviews

Nightly prices starting at

$40 before taxes and fees

Frequently Asked Questions

  • Do apartment rentals in New Windsor have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in New Windsor?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in apartment rentals in New Windsor?

    Experience the best of New Windsor with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in New Windsor have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in New Windsor?

    New Windsor has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in New Windsor have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in New Windsor?

    Yes! Work meets play with ease at over 20 vacation rentals in New Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in New Windsor?

    Four-legged friends are welcome in New Windsor. Choose from more than 10 vacation rentals for guests traveling with pets.

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