Milton Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Milton holiday rentals

Interior
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (32)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is HK$553
HK$1,388 total
includes taxes & fees
5 Jan - 6 Jan 2026
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Property grounds
Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge
Stone Ridge
9.0 out of 10, Wonderful, (15)
"Clean cozy will be staying again"
United States
Michael C.
The price is HK$455
HK$1,213 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Apartment with Sauna in Historic Stone Ridge
Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$735
HK$1,476 total
includes taxes & fees
26 Jan - 27 Jan 2026
Cozy 1-bedroom retreat minutes from West Point!
Terrace/patio
Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
The price is HK$455
HK$1,290 total
includes taxes & fees
5 Jan - 6 Jan 2026
Dream getaway apartment in the foot of Gunks Ridge
Fridge, microwave, oven, stovetop
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (4)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is HK$436
HK$1,778 total
includes taxes & fees
6 Jan - 7 Jan 2026
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (30)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is HK$552
HK$1,926 total
includes taxes & fees
6 Jan - 7 Jan 2026
Campfire Cottage: Fireplace, fire pit & no chores!
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is HK$856
HK$1,872 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Fridge, microwave, oven, stovetop
Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is HK$630
HK$2,299 total
includes taxes & fees
7 Jan - 8 Jan 2026
Retro Retreat: renovated 2BR, desk, no chore list!
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (5)
"Good stay, awesome place"
United States
Scott G.
The price is HK$755
HK$2,745 total
includes taxes & fees
4 Jan - 5 Jan 2026
House on the Babbling Brook- Quiet 2BR + King Bed!
Exterior
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (34)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
The price is HK$875
HK$2,085 total
includes taxes & fees
3 Jan - 4 Jan 2026
The Studio at the Inn at High Falls
Terrace/patio
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
2.0 star property
Gardiner
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is HK$826
HK$1,704 total
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (44)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is HK$869
HK$1,528 total
includes taxes & fees
5 Jan - 6 Jan 2026
Mid-Century DJ’s Dream
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is HK$855
HK$1,835 total
includes taxes & fees
7 Jan - 8 Jan 2026
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$996
HK$3,411 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,352
HK$3,496 total
includes taxes & fees
1 Jan - 2 Jan 2026
Rustic Cabin in Fishkill!
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is HK$716
HK$2,059 total
includes taxes & fees
6 Jan - 7 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Fridge, microwave, oven, stovetop
Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location
Poughkeepsie
6.8 out of 10, (5)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
United States
Andrea C.
The price is HK$701
HK$2,442 total
includes taxes & fees
21 Jan - 22 Jan 2026
Cozy Escape -Strong Wi-Fi -Prime Location
Fridge, microwave, oven, stovetop
Cozy Modern Stay - Walk to West Point & Main St!

Cozy Modern Stay - Walk to West Point & Main St!

Cozy Modern Stay - Walk to West Point & Main St!
2.0 star property
Highland Falls
The price is HK$614
HK$2,892 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Modern Stay - Walk to West Point & Main St!
Terrace/patio
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Highland
10.0 out of 10, Exceptional, (1)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is HK$1,283
HK$2,986 total
includes taxes & fees
5 Jan - 6 Jan 2026
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Fridge, microwave, oven, stovetop
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.4 out of 10, Exceptional, (12)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is HK$707
HK$1,560 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Milton Hotel Reviews

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

10/10 Excellent
"Changed room without any hassle "
Arthur 1-night trip
Posted 1 day ago
Courtyard by Marriott Poughkeepsie

Find out more about Milton

Search for holiday rentals in Milton on Expedia! You can easily find your home rentals, villas, holiday apartments in Milton using one of the methods below:

  • View our selection of featured holiday rentals in Milton
  • Use the map to find apartments and other holiday homes in the Milton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Milton while they last

Look no further and take a look at our great range of rental properties in Milton!

Frequently asked questions

Are there holiday rentals in Milton?

Yes, there are holiday rentals close to the most popular sights in Milton, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Milton is known for its spas and waterfalls. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Milton has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Milton offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Milton?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Milton stay.

What’s there to see and do in Milton?

Explore the area and family-friendly sights such as Mid-Hudson Civic Center, or get out into nature at a spot like Walkway Over the Hudson State Historic Park. Locust Grove and Mid-Hudson Bridge are a couple of places you'll find in the wider area.

What’s a holiday rental in Milton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Milton. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.