Milton Holiday Rentals

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Holiday Rentals in Milton

Outdoor dining
Black Walnut Tree Farm: Farmhouse on 50 Acres
10.0 out of 10, Exceptional, (13)
"Four friends had a wonderful time at Black Walnut Tree Farm. The space was amazing! There was plenty of spaces that we could hang out together, but also we each had areas that we could retreat to. The kitchen was well-stocked ands spacious, the large living room had many comfortable seats around the fire, and there was a great sunroom where we could sit and play games. The grounds were huge and one could easily get lost walking around the property. We all loved the place and are collectively...
Black Walnut Tree Farm: Farmhouse on 50 Acres
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (48)
"We thoroughly enjoyed our stay. It was a unique setting. Glen was very accommodating for our check in & out needs. Great location & central to everything we wanted to do & see. Definitely would come back."
The Farm at Hyde Park
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (36)
"This sweet little apartment was perfect for my solo stay. Comfortable, quiet, and very easy to get to. Lovely view from the deck. It had a feeling of security and privacy. Vicky was quick with answering my emails."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (21)
"place was great, exactly as described...ryan was great, no issues all was as described...however sent 2 notes via vrbo but rec'd no response and ryan apologized...so all good...if needed place up that way again would stay."
The price is NZ$456
includes taxes & fees
29 May - 30 May
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, (28)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is NZ$265
includes taxes & fees
3 Jun - 4 Jun
Cabin in the heart of the Hudson Valley, Cabin 2
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (21)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Beach
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (35)
"I needed a place in Wallkill NY to stay. This VRBO was perfect!"
The price is NZ$379
includes taxes & fees
18 Jun - 19 Jun
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, (168)
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"An unassuming setting belies the well-appointed interior and thoughtful extras you’ll find within. Parking is tight but it is off-street and the location offers come-and-go convenience for exploring the area."
The price is NZ$369
includes taxes & fees
2 Jun - 3 Jun
Campfire Cottage: Fireplace, fire pit & no chores!
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is NZ$505
includes taxes & fees
3 Jun - 4 Jun
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is NZ$265
includes taxes & fees
29 May - 30 May
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior
The Studio at the Inn at High Falls
8.4 out of 10, Very good, (17)
"Love staying at The Studio at the Inn at High Falls. It truly is my new home away from home. Soo Clean, Comfortable and incredible friendly helpful people who own and work there. Again Thank you Frank and too a New Year. Patricia"
The price is NZ$422
includes taxes & fees
2 Jun - 3 Jun
The Studio at the Inn at High Falls
Fridge, microwave, oven, stovetop
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay! We had a large group of 24 friends, and the house met all of our needs. It was very clean, had enough bedrooms for everyone, and a large dining table that accommodated everyone for big dinners. We spent a lot of time throughout the weekend outside playing lawn games and sitting by the fire. The place was close enough to grab amenities or go to a grocery store, but off the beaten path and quiet. It was exactly what was listed and made for a where enjoyable time....
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
Fridge, microwave, oven, stovetop
Historic Kingston 1800s Waterfront Townhouse - / Backyard / BKLYN Loft / Modern
9.8 out of 10, Exceptional, (24)
"We had a wonderful stay in Historic Kingston down by the riverfront. The property was perfect for our needs. A quiet side street offered close proximity to everything we needed. The unit was clean and well appointed. A whole house. Beautiful."
Historic Kingston 1800s Waterfront Townhouse - / Backyard / BKLYN Loft / Modern
4 bedrooms, WiFi, bed sheets
Bluming Fields - A private home on a 150-acre horse farm.
9.6 out of 10, Exceptional, (5)
"This is a beautiful home, well laid out, and perfect the needs of our group. The host was accommodating and responsive. I would definitely recommend!"
The price is NZ$956
includes taxes & fees
29 May - 30 May
Bluming Fields - A private home on a 150-acre horse farm.
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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.

Other types of properties in Milton you may be interested in

Terrace/patio
Buttermilk Falls Inn
3.0 star property
9.6 out of 10, Exceptional, (30)
"We liked everthing, the only problem was the air conditioner was loud, we did not like the pillows. The place was beautiful and the service was great, we would come back."
The price is NZ$613
includes taxes & fees
11 Jun - 12 Jun
Buttermilk Falls Inn
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1000)
"Will be returning..nice atmosphere "
The price is NZ$258
includes taxes & fees
3 Jun - 4 Jun
HYATT house Fishkill/Poughkeepsie
Suite, 2 Queen Beds, Non Smoking (Shower Only;with Sofabed)
Best Western Fishkill Inn & Suites
3.5 star property
8.6 out of 10, Excellent, (473)
"The glass doors to the first floor bedrooms did not have any privacy curtains."
The price is NZ$212
includes taxes & fees
5 Jun - 6 Jun
Best Western Fishkill Inn & Suites
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Milton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Milton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Milton. Seeing all the best attractions is bound to make you fall in love with Milton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Milton short-term rentals, that won’t be hard to do.

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?

The Farm at Hyde Park: This holiday home rental outside of Milton is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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. Poughkeepsie Galleria and Chance Theater 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.

Recent reviews of Milton properties
Expedia verified reviews