Jefferson Valley 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 Jefferson Valley vacation rentals

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

1. 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.
The price is CA $171
CA $422 total
includes taxes & fees
Nov 9 - Nov 10
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

2. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (42 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.
The price is CA $314
CA $559 total
includes taxes & fees
Nov 10 - Nov 11
Contemporary Cozy Cottage
Living area

3. 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.
The price is CA $144
CA $269 total
includes taxes & fees
Nov 8 - Nov 9
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.

4. 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.
The price is CA $463
CA $874 total
includes taxes & fees
Nov 19 - Nov 20
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

5. 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.
The price is CA $195
CA $604 total
includes taxes & fees
Nov 9 - Nov 10
Local Artist Inspired | Walk to WestPoint + King Bed
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.
The price is CA $191
CA $348 total
includes taxes & fees
Nov 8 - Nov 9
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

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

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is CA $199
CA $372 total
includes taxes & fees
Nov 10 - Nov 11
Perfect 2BR with Free Parking! Walk to West Point!
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

8. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is CA $179
CA $348 total
includes taxes & fees
Nov 8 - Nov 9
Mountain-View 2BR Steps from Thayer Gate
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

9. 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.
The price is CA $215
CA $409 total
includes taxes & fees
Nov 8 - Nov 9
Fabulous 3bdrm Home w/parking!
A blue house with a white porch, a welcome sign, and a mailbox.

10. 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.
The price is CA $196
CA $657 total
includes taxes & fees
Nov 11 - Nov 12
3BR West Point Retreat-3min to Back Gate+ King Bed
A wooden coffee table with two decorative planters in a living room.

11. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is CA $215
CA $379 total
includes taxes & fees
Nov 8 - Nov 9
Walk to WP Gate + Free Parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

12. 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.
The price is CA $215
CA $420 total
includes taxes & fees
Nov 8 - Nov 9
Lovely 3BR Home with parking-Walk to WP Gate!
A hallway with a wooden door, a black table with a sign, and large green plants.

13. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is CA $182
CA $588 total
includes taxes & fees
Nov 11 - Nov 12
3BR Near West Point | Coffee Bar | Sleeps 6
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

14. 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.
The price is CA $236
CA $376 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

15. 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.
The price is CA $277
CA $494 total
includes taxes & fees
Nov 12 - Nov 13
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is CA $255
CA $472 total
includes taxes & fees
Nov 10 - Nov 11
Hudson Valley/West Point Retreat w/ parking!
A stone staircase leading to a house with a stone wall and a metal gate.

17. 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.
The price is CA $349
CA $539 total
includes taxes & fees
Nov 10 - Nov 11
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

18. 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.
The price is CA $233
CA $472 total
includes taxes & fees
Nov 12 - Nov 13
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

19. '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.
The price is CA $349
CA $610 total
includes taxes & fees
Nov 19 - Nov 20
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A brick building with a sign reading 'Lobby' in front.

20. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is CA $111
CA $128 total
includes taxes & fees
Nov 24 - Nov 25
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
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 Jefferson Valley Hotel Reviews

A buffet with various food items, including omelets and baked goods, served in metal containers.
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Peekskill

10/10 Excellent

We enjoyed our stay very much. It was lovely.
Canada
Blair
Reviewed November 6, 2025
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Find out more about Jefferson Valley

Everything you need to know about Jefferson Valley 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 Jefferson Valley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Jefferson Valley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jefferson Valley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jefferson Valley. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jefferson Valley vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jefferson Valley vacation rentals we have selected for you start as low as CA $143 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jefferson Valley rentals

At Expedia, we put the best Jefferson Valley 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 Jefferson Valley 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 Jefferson Valley 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 Jefferson Valley. 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

Can I find a vacation rental in Jefferson Valley?

Yes, you can find vacation rentals close to well known sights in Jefferson Valley, or you can select a secluded option if you're looking for a relaxing stay. Jefferson Valley is known for its shopping.

What are some of the best vacation home rentals that Jefferson Valley has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near Jefferson Valley 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 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 Jefferson Valley?

Explore the area and family-friendly sights such as SplashDown Beach, or get out into nature at a spot like Lake Mahopac. In the larger area, you’ll find Jefferson Valley Mall and Franklin D. Roosevelt State Park.

What’s a vacation rental in Jefferson Valley like?

Vacation rentals are private properties you can book for short or long periods in Jefferson Valley. Vacation rentals provide amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips.