Heritage Hills Holiday Rentals

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Holiday Rentals in Heritage Hills

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, 96 reviews
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$459
per night
10 Jun - 11 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, 35 reviews
"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
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 75 reviews
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
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Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, 62 reviews
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 35 reviews
"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
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 59 reviews
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, 18 reviews
"My husband, dog and I had a great Memorial Day weekend at this lakeside property. The house is a short drive away from NYC and is situated perfectly between the quaint towns of Ridgefield and Katonah. We had a good time enjoying the lake and nearby hikes."
Serenity Awaits at this Cozy Lakeside Bungalow
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, 22 reviews
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, 18 reviews
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
The price is NZ$2,081
per night
2 Jul - 3 Jul
Lakeview Estate - Chef's Kitchen - NYC Getaway
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, 21 reviews
"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
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 168 reviews
"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!
Lakefront New York Abode w/ Deck, Grill & Fire Pit
9.6 out of 10, Exceptional, 4 reviews
"we were able to have all 3 of our children, with 2 of their spouses and bridal party for my daughter stay with us for the weekend. There were plenty of things to entertain during downtime. Rooms were comfortable and location was convenient to wedding activities."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, 18 reviews
"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$515
per night
17 Jun - 18 Jun
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, 8 reviews
"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
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, 31 reviews
"We came for West Point graduation. It was perfect in its location to West Point. Beds were good, its was very clean, and the hot tub was great! The owners communicated well and helped us with our scheduling. We highly recommend this place!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, 17 reviews
"Gorgeous, as advertised!"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
10.0 out of 10, Exceptional, 3 reviews
"This enchanting place was everything we wanted and more. Not only was it completely adorable, very clean, and had an extraordinary shower, it was in the heart of everything. We walked everywhere and had the best time. The amazing host, Aldo, was so gracious and took great care of us. I will definitely book here for my next trip to Beacon."
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.6 out of 10, Exceptional, 20 reviews
"We came for a girls weekend. The house is beautiful with plenty of comfy seating. Super clean. The view is beautiful and fun to watch all the boaters. We could not get fire pit to work, but this could have been user error. I would caution others that the stairs are a lot! Definitely not for elders and a real workout, but this was clearly stated in description. Otherwise an absolute dream house with plenty of space. The attention to detail and decor (especially in the bathrooms) was appreciated!...
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Private room in a single family house near Peekskill
9.8 out of 10, Exceptional, 13 reviews
"My wife and I enjoyed our stay. Property owner was very responsive to questions. Home was very clean and inviting. We loved the cats!"
The price is NZ$231
per night
11 Jun - 12 Jun
Private room in a single family house near Peekskill
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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 Heritage Hills you may be interested in

Ethan Allen Hotel
3.5 star property
7.8 out of 10, Good, 1,000 reviews
"Wonderful hotel "
The price is NZ$235
per night
10 Jun - 11 Jun
Ethan Allen Hotel
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, 1,005 reviews
"N/A"
The price is NZ$256
per night
12 Jun - 13 Jun
HYATT house Fishkill/Poughkeepsie
Best Western Fishkill Inn & Suites
3.5 star property
8.6 out of 10, Excellent, 482 reviews
"We enjoyed very much our stay here, the outdoor pool was the best for my kids:) everything was with a very short distance from food to shopping . Close to the outlets. We love it. "
The price is NZ$212
per night
1 Jul - 2 Jul
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 Heritage Hills 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 Heritage Hills. 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 Heritage Hills. Seeing all the best attractions is bound to make you fall in love with Heritage Hills. 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 Heritage Hills short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Heritage Hills?

Yes, there are holiday rentals close to the most popular sights in Heritage Hills, or you can select a more secluded option if you're looking for a relaxing stay. Heritage Hills is known for its cathedral and lake views. Make sure you have time to check out the basketball games while you're in the area.

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

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Heritage Hills is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Heritage Hills?

Explore the area and family-friendly sights such as Grand Prix New York / Spins Bowl, or get out into nature at a spot like Lake Mahopac. In the wider area, you’ll find Putnam County Golf Course and Jefferson Valley Mall.

What’s a holiday rental in Heritage Hills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Heritage Hills. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family getaway.

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