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Jefferson Valley Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Jefferson Valley holiday rentals

Exterior detail

1. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (24 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,238
HK$3,767 total
includes taxes & fees
3 Sept - 4 Sept
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Exterior detail

2. West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking

West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Highland Falls
9.4 out of 10, Exceptional, (30 reviews)
"Our stay was excellent! Extremely clean, everything we needed. Walkable to everything in town. Great communication work h Host. We will definitely be staying again. "
United States
Joelle M.
The price is HK$2,548
HK$4,204 total
includes taxes & fees
30 Aug - 31 Aug
West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Private kitchen

3. 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 HK$1,919
HK$3,149 total
includes taxes & fees
1 Sept - 2 Sept
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Exterior

4. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,371
HK$3,606 total
includes taxes & fees
17 Sept - 18 Sept
Rustic Cabin in Fishkill!
Outdoor dining

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
The price is HK$2,007
HK$4,310 total
includes taxes & fees
15 Sept - 16 Sept
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Interior

6. 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 HK$1,274
HK$2,550 total
includes taxes & fees
30 Aug - 31 Aug
Lovely 3BR Home with parking-Walk to WP Gate!
Property grounds

7. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (141 reviews)
"We had a great stay!!"
United States
Jasmine
The price is HK$1,552
HK$2,630 total
includes taxes & fees
3 Sept - 4 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Living area

8. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (25 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is HK$1,141
HK$2,132 total
includes taxes & fees
31 Aug - 1 Sept
Walk to WP Gate + Free Parking!
Living area

9. Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
The price is HK$4,696
HK$8,233 total
includes taxes & fees
31 Aug - 1 Sept
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Exterior detail

10. 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 HK$1,334
HK$2,563 total
includes taxes & fees
30 Aug - 31 Aug
Fabulous 3bdrm Home w/parking!
Living area

11. 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
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$2,011
HK$3,658 total
includes taxes & fees
8 Sept - 9 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Dining

12. 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, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is HK$1,261
HK$2,670 total
includes taxes & fees
2 Sept - 3 Sept
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Living area

13. '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, (7 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 HK$1,872
HK$3,504 total
includes taxes & fees
15 Sept - 16 Sept
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Exterior

14. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is HK$3,881
HK$5,580 total
includes taxes & fees
31 Aug - 1 Sept
Chestnut on Willow Lake
Outdoor dining

15. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (74 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is HK$2,048
HK$2,703 total
includes taxes & fees
3 Sept - 4 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Private kitchen

16. Private Country Getaway

Private Country Getaway
Bedford Hills
9.6 out of 10, Exceptional, (4 reviews)
"We had a busy and lovely weekend to attend and be part of my nieces wedding. The location was perfect and the property is beautiful. Kitchen was perfect for gathering in the morning and the great room was big and comfy for catching up! "
United States
Karin R.
The price is HK$9,406
HK$15,304 total
includes taxes & fees
10 Sept - 11 Sept
Private Country Getaway
Living area

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Visiting West Point for ring weekend. Location was great and the reason we chose the place. Property itself could really use some TLC, but it met our needs. Communication with the owner was good and gaining access to the property was straightforward. Would consider staying here again just based on the close proximity to West Point."
United States
Kevin
The price is HK$1,104
HK$2,001 total
includes taxes & fees
1 Sept - 2 Sept
Cozy 1-bedroom retreat minutes from West Point!
Exterior detail

18. Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi

Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Highland Falls
9.6 out of 10, Exceptional, (36 reviews)
"Good location and had a great stay!"
United States
James M.
The price is HK$2,548
HK$4,576 total
includes taxes & fees
30 Aug - 31 Aug
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Private kitchen

19. 2-bedroom apartment in excellent Newburgh with AC and charm

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (3 reviews)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
The price is HK$1,481
HK$1,915 total
includes taxes & fees
11 Sept - 12 Sept
2-bedroom apartment in excellent Newburgh with AC and charm
Living area

20. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is HK$3,128
HK$8,096 total
includes taxes & fees
26 Sept - 27 Sept
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
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

Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel

8/10 Good
"I had an amazing time the hot tub was clean staff was helpful Food was good expensive but good I which the pool was bigger but overall good daycation"
Desorene 1-night trip
Posted 8 hours ago
Sheraton Tarrytown Hotel

Find out more about Jefferson Valley

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

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

Frequently asked questions

Can I find a holiday rental in Jefferson Valley?

Yes, there are holiday rentals close to the most popular sights in Jefferson Valley, or you can select a more secluded option if you're looking for a relaxing stay. Jefferson Valley is known for its shopping.

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of 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 an electric kettle, so that 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 wider area, you’ll find Jefferson Valley Mall and Franklin D. Roosevelt State Park.

What’s a holiday rental in Jefferson Valley like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Jefferson Valley. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.