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Heritage Hills Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Heritage Hills vacation rentals

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

1. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$301 nightly
The price is $326
Nov 9 - Nov 10
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

2. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
7.4 out of 10, Good, (3 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
$163 nightly
The price is $177
Nov 9 - Nov 10
Total with taxes and fees
Welcome to Sweet Abby Rose!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

3. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
$341 nightly
The price is $390
Nov 10 - Nov 11
Total with taxes and fees
Contemporary Cozy Cottage
A historic building with a central tower labeled 'West Point Museum,' featuring a traditional architectural style with multiple windows and a stone facade.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$283 nightly
The price is $286
Nov 9 - Nov 10
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

5. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
$231 nightly
The price is $261
Nov 9 - Nov 10
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

6. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
$233 nightly
The price is $258
Nov 9 - Nov 10
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

7. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
$274 nightly
The price is $302
Nov 9 - Nov 10
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

8. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$274 nightly
The price is $311
Nov 9 - Nov 10
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

9. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$397 nightly
The price is $401
Nov 11 - Nov 12
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A nighttime view of a residential street with houses, trees, and parked cars.

10. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
$309 nightly
The price is $354
Nov 12 - Nov 13
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Living area

11. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$178 nightly
The price is $195
Dec 8 - Dec 9
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

12. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
$550 nightly
The price is $607
Nov 10 - Nov 11
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

13. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
$233 nightly
The price is $257
Nov 9 - Nov 10
Total with taxes and fees
Mountain-View 2BR Steps from Thayer Gate
A blue house with a white porch, a welcome sign, and a mailbox.

14. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
$390 nightly
The price is $443
Nov 11 - Nov 12
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
A stone staircase leading to a house with a stone wall and a metal gate.

15. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
$343 nightly
The price is $392
Nov 9 - Nov 10
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

16. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
$233 nightly
The price is $257
Nov 9 - Nov 10
Total with taxes and fees
Perfect 2BR with Free Parking! Walk to West Point!
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

17. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (9 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
$371 nightly
The price is $424
Nov 19 - Nov 20
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A modern kitchen with wooden cabinets, a stainless steel stove, a microwave, and a toaster. There are stools and a small island with a plant.

18. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean, modern, functional, comfortable. Great stay"
United States
Jerell T.
$253 nightly
The price is $281
Nov 9 - Nov 10
Total with taxes and fees
Walk to WP Gate + Free Parking!
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

19. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (5 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$464 nightly
The price is $525
Nov 11 - Nov 12
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

20. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
$286 nightly
The price is $325
Nov 9 - Nov 10
Total with taxes and fees
Hudson Valley/West Point Retreat w/ parking!
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.
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Top Heritage Hills Hotel Reviews

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

10/10 Excellent
"We enjoyed our stay. It was remarkably quiet. No road noise, no noise from neighboring rooms!"
Danielle 2-night trip
Posted 5 hours ago
Comfort Suites Fishkill near Interstate 84

Find out more about Heritage Hills

Everything you need to know about Heritage Hills vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Heritage Hills vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Heritage Hills vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Heritage Hills vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Heritage Hills. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Heritage Hills in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $91 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Heritage Hills rentals

At Expedia, we put the best Heritage Hills vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Heritage Hills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Heritage Hills vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Heritage Hills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Heritage Hills?

Yes, there are vacation rentals close to the most popular local attractions in Heritage Hills, or you can select a secluded option if you want a relaxing place to 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's the top vacation rental in Heritage Hills?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Heritage Hills offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 larger area, you’ll find Putnam County Golf Course and Old Salem Farm.

What’s a vacation rental in Heritage Hills like?

A vacation rental is a private property you can book for a long or short time in Heritage Hills. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a small group gathering.