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

Guest suite in Montgomery

4.95 out of 5 average rating, 417 reviews

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

Nov 10 – 17

€ 129 per night
Guest favorite

Guest suite in Chester

4.96 out of 5 average rating, 224 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Jan 4 – 11

€ 104 per night
Guest favorite

Apartment in New Paltz

4.96 out of 5 average rating, 343 reviews

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 11 – 18

€ 107 per night

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

Cottage in Newburgh

4.88 out of 5 average rating, 184 reviews

Cozy Lake Cottage

Apr 16 – 23

€ 118 per night
Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 738 reviews

Hudson Valley Tiny House

Jun 11 – 18

€ 112 per night
Guest favorite

Guest suite in Newburgh

4.99 out of 5 average rating, 152 reviews

Salvick House, Central to all Bethels

Mar 13 – 20

€ 174 per night
Guest favorite

Apartment in Cold Spring

4.95 out of 5 average rating, 515 reviews

Beautiful loft space

Feb 22 – Mar 1

€ 188 per night
Superhost

Apartment in Newburgh

4.91 out of 5 average rating, 243 reviews

Victorian Charmer with Private Balcony

Apr 17 – 24

€ 201 per night
Guest favorite

Tiny home in Marlboro

4.93 out of 5 average rating, 216 reviews

Cozy 1860's Cottage Near Weeds Orchards,Glorie Fms

Feb 2 – 9

€ 113 per night
Guest favorite

Cottage in Goshen

4.94 out of 5 average rating, 187 reviews

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

Nov 14 – 21

€ 140 per night
Guest favorite

Tiny home in Wallkill

4.99 out of 5 average rating, 198 reviews

Get Away to "Hygge" Tiny House on 75 Private Acres

Jun 11 – 18

€ 201 per night
Guest favorite

Apartment in Newburgh

4.85 out of 5 average rating, 140 reviews

#1, Historic Studio, Newburgh, Beacon, West Point

Sep 10 – 17

€ 127 per night
Guest favorite

Home in New Windsor

5.0 out of 5 average rating, 43 reviews

Cozy cottage with hot tub and game room

Dec 5 – 12

€ 299 per night
Guest favorite

Apartment in Newburgh

4.9 out of 5 average rating, 77 reviews

Bright and Stylish 1-bedroom Apartment

Apr 17 – 24

€ 143 per night
Guest favorite

Guest suite in Cornwall-on-Hudson

4.88 out of 5 average rating, 43 reviews

The Nest at Sparrow House NY-Cozy Artist's Studio

Dec 15 – 22

€ 162 per night

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

€ 37 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 Apartment Rentals in New Windsor?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 20 homes with a kitchen, over 10 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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

    Experience the best of New Windsor with our house rentals, starting at about $60 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.

Destinations to explore

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