Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Sleepy Hollow vacation rentals

Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (25 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is AED 1,594
AED 3,329 total
includes taxes & fees
14 Jun - 15 Jun
Waterview House Walking Distance from Cove Beach
Fridge, microwave, oven, stovetop

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is AED 2,156
AED 4,022 total
includes taxes & fees
3 Jun - 4 Jun
Stylish Beach Home near Stamford Downtown/Beach
TV

Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking

Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking
Cove - East Side - Shippan
8.0 out of 10, Very Good, (6 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is AED 757
AED 1,577 total
includes taxes & fees
29 Jun - 30 Jun
Stamford Hideaway w/ Fire Pit
Smart TV, fireplace, stereo, offices

The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
Cove - East Side - Shippan
9.0 out of 10, Wonderful, (10 reviews)
"Beautiful place, very clean. Great Host!"
United States
Alejandro A.
The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
TV, fireplace, foosball, offices

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
The price is AED 2,251
AED 4,364 total
includes taxes & fees
4 Jun - 5 Jun
New Beach Home near Stamford Downtown/Shippan
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (123 reviews)
"Was a good Hotel friendly and clean"
United States
Tamara
The price is AED 547
AED 629 total
includes taxes & fees
3 Jun - 4 Jun
Stamford Suites
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is AED 588
AED 1,208 total
includes taxes & fees
29 Jun - 30 Jun
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Smart TV

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is AED 529
AED 1,537 total
includes taxes & fees
4 Jun - 5 Jun
Modern Luxe 1BR Apt in Downtown Stamford
Offices

Penthouse Perfection: with Unmatched Skyline Views

Penthouse Perfection: with Unmatched Skyline Views
Downtown Stamford
10.0 out of 10, Exceptional, (13 reviews)
"The place met all of our needs. Centrally located, easy to access and perfectly clean. We all enjoyed our stay."
United States
Gene A.
The price is AED 1,230
AED 2,203 total
includes taxes & fees
21 Jun - 22 Jun
Penthouse Perfection: with Unmatched Skyline Views
TV, stereo

Solara – Luxury 1BR Downtown

Solara – Luxury 1BR Downtown
Downtown Stamford
The price is AED 772
AED 1,567 total
includes taxes & fees
4 Jun - 5 Jun
Solara – Luxury 1BR Downtown
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.2 out of 10, Wonderful, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AED 753
AED 1,439 total
includes taxes & fees
17 Jun - 18 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Interior

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
West Side
9.4 out of 10, Exceptional, (6 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is AED 1,539
AED 2,747 total
includes taxes & fees
10 Jun - 11 Jun
Walkable Townhouse with Garage & Yard, 45 min to NYC!
Interior

The Gallery in Downtown Stamford

The Gallery in Downtown Stamford
Downtown Stamford
10.0 out of 10, Exceptional, (5 reviews)
"Great location in Downtown Stamford. "
United States
Jim W.
The price is AED 951
AED 1,799 total
includes taxes & fees
14 Jun - 15 Jun
The Gallery in Downtown Stamford
Property grounds

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, (36 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AED 615
AED 1,177 total
includes taxes & fees
10 Jun - 11 Jun
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is AED 808
AED 1,538 total
includes taxes & fees
8 Jun - 9 Jun
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Property grounds

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (7 reviews)
"The location was perfect for our family getaway. The snow and river backdrop brought the holiday spirit out in our college age kids. There was plenty of room and the fireplace was great. All the appliances are high end and the communication was excellent. The host went out of his way to make the visit special. Would highly recommend "
United States
Scott and Linsay T.
The price is AED 1,967
AED 4,677 total
includes taxes & fees
3 Jun - 4 Jun
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Apartment (1 Bedroom) | Interior

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is AED 742
AED 1,615 total
includes taxes & fees
5 Jun - 6 Jun
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Property grounds

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 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...
United States
Kathleen W.
The price is AED 826
AED 1,101 total
includes taxes & fees
4 Jun - 5 Jun
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Interior

Mansion in Greenwich with private lake and river

Mansion in Greenwich with private lake and river
Greenwich
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home. Exquisite decor and our kids enjoyed fishing right out back. Thoroughly enjoyed. "
United States
J.J. O.
The price is AED 13,774
AED 19,022 total
includes taxes & fees
22 Jun - 23 Jun
Mansion in Greenwich with private lake and river
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 Sleepy Hollow Hotel Reviews

Royal Regency Hotel

Royal Regency Hotel

10/10 Excellent
"I would recommend to everyone to go there"
Ilir 2-night trip
Posted 2 hours ago
Royal Regency Hotel

Frequently asked questions

Can I find a vacation rental in Sleepy Hollow?

Yes, there are vacation rentals near the most popular sights in Sleepy Hollow, or you can go with a more secluded option if you're looking for relaxation. Sleepy Hollow is known for its churches and local tours. Make sure you have time to check out the riverfront and restaurants during your trip.

What are some of the best vacation rentals in Sleepy Hollow?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This vacation home rental outside of Sleepy Hollow is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease 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. You and your friends and family can relax into your vacation with amenities like foosball.

How many vacation rentals are there in Sleepy Hollow?

Choose from 3 Expedia vacation rentals in Sleepy Hollow for a memorable vacation.

What can I see and do in Sleepy Hollow?

While exploring the area, visit family-friendly sights like Bronx Zoo, or get outside and enjoy nature at Rockefeller State Park Preserve. Other places in town to visit include Philipsburg Manor and Old Dutch Church of Sleepy Hollow.

What are vacation rentals like in Sleepy Hollow?

Vacation rentals are private accommodations you can reserve for several days or longer in Sleepy Hollow. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.