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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Chappaqua vacation rentals
1. Summer Pool Oasis Custom Bar Arcade Pool Table
Summer Pool Oasis Custom Bar Arcade Pool TableOssining
$947 nightly
The price is $1,054
Nov 16 - Nov 17
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.
$765 nightly
The price is $781
Nov 16 - Nov 17
Total with taxes and fees
3. 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.
$343 nightly
The price is $392
Nov 10 - Nov 11
Total with taxes and fees
4. Stamford Suites
Stamford SuitesDowntown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
Christine
$164 nightly
The price is $189
Nov 10 - Nov 11
Total with taxes and fees
5. 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.
$312 nightly
The price is $357
Nov 12 - Nov 13
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.
$371 nightly
The price is $424
Nov 19 - Nov 20
Total with taxes and fees
7. 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
$111 nightly
The price is $127
Nov 10 - Nov 11
Total with taxes and fees
8. 1BR Queen near NYC | Trails, Biking & Sauna Bliss
1BR Queen near NYC | Trails, Biking & Sauna BlissOssining
$265 nightly
The price is $295
Nov 15 - Nov 16
Total with taxes and fees
9. 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.
$289 nightly
The price is $330
Nov 10 - Nov 11
Total with taxes and fees
10. 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.
$245 nightly
The price is $280
Nov 10 - Nov 11
Total with taxes and fees
11. Guesthouse at Norwalk Inn
Guesthouse at Norwalk InnHistoric District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
anthony
$275 nightly
The price is $316
Dec 2 - Dec 3
Total with taxes and fees
12. 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
$114 nightly
The price is $130
Nov 10 - Nov 11
Total with taxes and fees
13. 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
$116 nightly
The price is $133
Nov 10 - Nov 11
Total with taxes and fees
14. Piermont Oasis
Piermont OasisPiermont
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
Megan D.
$175 nightly
The price is $195
Nov 16 - Nov 17
Total with taxes and fees
15. 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 10 - Nov 11
Total with taxes and fees
16. 1 Queen Bed | Non-Smoking
1 Queen Bed | Non-SmokingElmsford
8.0 out of 10, Very good, (6 reviews)
$111 nightly
The price is $127
Nov 10 - Nov 11
Total with taxes and fees
17. 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 10 - Nov 11
Total with taxes and fees
18. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!Port Chester
10.0 out of 10, Exceptional, (34 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
Sarah W.
$335 nightly
The price is $383
Nov 10 - Nov 11
Total with taxes and fees
19. Gem by the water+ firepit and all fenced backyard
Gem by the water+ firepit and all fenced backyardWaterside
10.0 out of 10, Exceptional, (21 reviews)
"Property was exactly what we needed for our stay"
Christopher E.
$379 nightly
The price is $434
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
8.0 out of 10, Very good, (4 reviews)
"Price was right for the stay! I would come back"
Mark
$413 nightly
The price is $472
Nov 10 - Nov 11
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 Chappaqua 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
