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Find Vacation Homes in Town of Lewisboro, NY from $141

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Top Cities in Town of Lewisboro

Vacation Homes in Town of Lewisboro

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
$190 nightly
The price is $215
Nov 16 - Nov 17
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction
8.8 out of 10, Excellent, (44)
"A nice location near many parks and lake beaches. Modern decor, appliances and fixtures. The driveway REALLY is NOT hospitable. The kitchen is missing things like measuring tools/serving spoons/serving bowls. A safety note: the stairs both going from the kitchen to the bedrooms and to the sunken dining area are not spaced proportionally and could be a hazard for some."
United States
Joanna B.
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Very nice stay and very clean"
United States
Markel W.
$125 nightly
The price is $141
Nov 16 - Nov 17
Total with taxes and fees
Business or Weekend escape

Hickory on Willow Lake

Fishkill
9.6 out of 10, Exceptional, (4)
"We stayed one night. Would loved to have stayed longer. Beautiful property. "
United States
Christine B.
$646 nightly
The price is $736
Nov 24 - Nov 25
Total with taxes and fees
Hickory on Willow Lake

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Ossining
9.0 out of 10, Wonderful, (6)
"This is an incredibly unique property with some upsides. It is a cool old (1920's) Tudor style house that is well-suited for large groups. While it was fine for a couple of nights, any longer would have made the downsides (deferred maintenance, insufficient silverware, stained carpeting) less tolerable. There were also some communication issues with the property management company and the host during the stay. Specifically, we counted on there being a crib available, as it was specified in the...
United States
Marnie O.
$881 nightly
The price is $905
Nov 16 - Nov 17
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield
9.2 out of 10, Wonderful, (32)
"I stayed here for three nights with my elderly mom. The home is lovely and very comfortable, with lovely linens, updated bathrooms, and luxurious beds. The kitchen is wonderfully equipped for anything you might want to prepare. This would be an excellent spot for a family with children. The hosts were very responsive and gracious. Above all else, the view is absolutely spectacular. I wish i could wake up to it every day. I hope to go back in the fall when the leaves are changing. Highly...
United States
Virginia F.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel Hamlet
10.0 out of 10, Exceptional, (94)
"We loved our stay. It was great for a family Thanksgiving"
United States
Edmund F.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

New Fairfield
10.0 out of 10, Exceptional, (14)
"Was a great find. Updated, spacious and clean."
United States
Paul B.
$444 nightly
The price is $503
Nov 16 - Nov 17
Total with taxes and fees
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Stay at Black Rock Harbor

Black Rock Historic District
10.0 out of 10, Exceptional, (24)
"We enjoyed this beautiful home and appreciated the many touches that made our stay enjoyable!"
United States
Nancy J.
Stay at Black Rock Harbor

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

Waterside
10.0 out of 10, Exceptional, (6)
"Exceptional space for our needs. We’d absolutely book again if the opportunity arises. Maritza was communicative and everything was easily accessible"
United States
Joanne
$294 nightly
The price is $332
Nov 17 - Nov 18
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Spacious 4-bedroom house in charming Rye with AC

Rye
$2,502 nightly
The price is $2,502
Nov 14 - Nov 15
Total with taxes and fees
Spacious 4-bedroom house in charming Rye with AC

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Brookfield
9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Nyack
9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
United States
Dr. Andrea W.
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Bridgeport
9.6 out of 10, Exceptional, (4)
"Extremely clean and well prepared home stocked with items we may need. Plenty of space for all guests. Comfortable beds. Felt safe with the use of electronic keypad entry and security system. Very well maintained. Historic feel with modern amenities. Great location in regards to where we needed to be. Able to communicate with host who assisted in accommodations. Plenty of parking. Lovely place. "
United States
natalie c.
$1,222 nightly
The price is $1,383
Nov 14 - Nov 15
Total with taxes and fees
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Peaceful Vintage Home with Private Lake in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Property was beautiful in a very quiet and peaceful area. Our host Kadriia was so amazing and would respond so quickly to any questions we had and communicated clearly. My wife and our friends had a Halloween themed wedding party for our friends who couldn’t make it to the actual wedding and we couldn’t have had a better time. "
United States
Connor K.
$518 nightly
The price is $587
Nov 16 - Nov 17
Total with taxes and fees
Peaceful Vintage Home with Private Lake in Redding, CT.

Luxury NY Home with Game Room & Free Parking

2.0 star property
White Plains
6.0 out of 10, (1)
"Comfortable bedrooms, clean room. Need to make few updates to make it kids friendly (for example adding covers to the stove), adding dishes and cups. Advising is an apartment and not a house. Neighborhood is convenient to highways, trains and city center."
United States
Betty A.
Luxury NY Home with Game Room & Free Parking

Charming 3-bedroom house with WiFi, AC in serene Fairfield

Fairfield
9.0 out of 10, Wonderful, (9)
"No complaints here, it was a nice house in a quiet neighborhood! I would visit again when the time is right! "
United States
Sharon O.
Charming 3-bedroom house with WiFi, AC in serene Fairfield

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls
10.0 out of 10, Exceptional, (3)
"Good stay, awesome place"
United States
Scott G.
$396 nightly
The price is $422
Nov 23 - Nov 24
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Stylish Beach Home near Stamford Downtown/Beach

Cove - East Side - Shippan
10.0 out of 10, Exceptional, (23)
"We had an absolutely amazing time during our stay. The house was beautiful, and Elena was super quick & helpful with answering any questions we had. Both the check in and check out processes were easy and smooth. We had a great time and would highly recommend staying here!"
United States
Matthew O.
$736 nightly
The price is $783
Nov 18 - Nov 19
Total with taxes and fees
Stylish Beach Home near Stamford Downtown/Beach

Historic Hideaway with Lake Access!

South Salem
9.8 out of 10, Exceptional, (20)
"We were in town for work for the week and found this site online. Great spot, nice a quiet. "
United States
Andy R.
Historic Hideaway with Lake Access!
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 Town of Lewisboro Hotel Reviews

Find out more about Town of Lewisboro

Booking Tips to Find the Best Town of Lewisboro Vacation Homes


How much does it cost to rent a vacation home in Town of Lewisboro?

You can find incredible Town of Lewisboro vacation homes for all types of budgets: between $141 and $2,502 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Town of Lewisboro?

If you are looking for a great deal on your vacation home in Town of Lewisboro, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Town of Lewisboro?

There are 408 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Town of Lewisboro?

Begin by entering your trip dates to see what type of Town of Lewisboro rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Town of Lewisboro?

Booking Town of Lewisboro vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Town of Lewisboro rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Town of Lewisboro along with your vacation property, into a Town of Lewisboro vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Town of Lewisboro Vacation Homes information

Number of reviews
351
Accommodation
408 Vacation Homes
Lowest Price
$141
Highest Price
$2,502

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