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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Ossining vacation rentals
1. Summer Pool Oasis Custom Bar Arcade Pool Table
Summer Pool Oasis Custom Bar Arcade Pool TableOssining
$916 nightly
The price is $1,020
Nov 9 - Nov 10
Total with taxes and fees
2. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
Karen O.
$758 nightly
The price is $774
Nov 9 - Nov 10
Total with taxes and fees
3. 1BR Queen near NYC | Trails, Biking & Sauna Bliss
1BR Queen near NYC | Trails, Biking & Sauna BlissOssining
$262 nightly
The price is $292
Nov 15 - Nov 16
Total with taxes and fees
4. Polished 1BR w/ Accessible Room Features + Sauna
Polished 1BR w/ Accessible Room Features + SaunaOssining
6.0 out of 10, (1 review)
"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "
Nada S.
$262 nightly
The price is $292
Nov 15 - Nov 16
Total with taxes and fees
5. 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. "
Eva C.
$353 nightly
The price is $404
Nov 9 - Nov 10
Total with taxes and fees
6. '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. "
Mateo A.
$382 nightly
The price is $437
Nov 19 - Nov 20
Total with taxes and fees
7. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Comfortable 2bd - Convenience & Style - 45min to NYC - Great FoodCROTON 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."
Margaret S.
$309 nightly
The price is $354
Nov 12 - Nov 13
Total with taxes and fees
8. 1 Queen Bed | Smoking
1 Queen Bed | SmokingElmsford
10.0 out of 10, Exceptional, (1 review)
"Beds were adequate, nothing special but perfectly fine for a short overnight stay."
Anonymous traveler
$116 nightly
The price is $133
Nov 10 - Nov 11
Total with taxes and fees
9. Piermont Oasis
Piermont OasisPiermont
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
Megan D.
$180 nightly
The price is $200
Nov 16 - Nov 17
Total with taxes and fees
10. Contemporary Cozy Cottage
Contemporary Cozy CottageLake 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."
Heather M.
$350 nightly
The price is $400
Nov 10 - Nov 11
Total with taxes and fees
11. Stamford Suites
Stamford SuitesDowntown Stamford
6.2 out of 10, (207 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
Christine
$149 nightly
The price is $171
Nov 17 - Nov 18
Total with taxes and fees
12. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding HighlandsFort Montgomery
9.8 out of 10, Exceptional, (150 reviews)
"We had a great stay!!"
Jasmine
$267 nightly
The price is $315
Dec 7 - Dec 8
Total with taxes and fees
13. 3BR Prime Luxury NY - Free Parking
3BR Prime Luxury NY - Free ParkingWhite Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
Osmond
$1,134 nightly
The price is $1,263
Nov 7 - Nov 8
Total with taxes and fees
14. 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. "
Andrew L.
$294 nightly
The price is $299
Nov 9 - Nov 10
Total with taxes and fees
15. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.Greenwich
9.8 out of 10, Exceptional, (46 reviews)
"Nice stay"
Christopher J.
$297 nightly
The price is $338
Nov 7 - Nov 8
Total with taxes and fees
16. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Private Gazebo on Byram River, Naturally Preserved your own stone deck GreenwichGreenwich
8.6 out of 10, Excellent, (7 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
Kathleen W.
$252 nightly
The price is $287
Nov 7 - Nov 8
Total with taxes and fees
17. 3BR Near West Point | Coffee Bar | Sleeps 6
3BR Near West Point | Coffee Bar | Sleeps 6Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Clean and convenient near West Point golf course"
mario b.
$411 nightly
The price is $418
Nov 11 - Nov 12
Total with taxes and fees
18. 1 King Bed | Non-Smoking
1 King Bed | Non-SmokingElmsford
10.0 out of 10, Exceptional, (2 reviews)
"Our rooms felt cozy enough for two people with decent privacy due to separate bathrooms nearby too.The location suited our plan moving between airport runs & visits close by malls perfectly."
Anonymous traveler
$119 nightly
The price is $136
Nov 10 - Nov 11
Total with taxes and fees
19. 2 Full Beds | Non-Smoking
2 Full Beds | Non-SmokingElmsford
10.0 out of 10, Exceptional, (1 review)
"The staff were attentive without being pushy, and the bed provided good comfort."
Anonymous traveler
$122 nightly
The price is $140
Nov 10 - Nov 11
Total with taxes and fees
20. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!Greenwich
$439 nightly
The price is $505
Nov 7 - Nov 8
Total with taxes and fees
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 Ossining Hotel Reviews
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Holiday Inn Express & Suites Hawthorne Elmsford North by IHGHawthorne
10/10 Excellent
The room was very clean and the hotel itself looked very clean. Beds were comfortable and the room was very spacious. I would definitely recommend this hotel to anyone staying in this area.
Lorena
