A calm lake reflecting a forested hill during sunset.

Vacation Rentals in Town of Lewisboro

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Our top choices for Town of Lewisboro vacation rentals

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (111 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ¥28,062
¥41,983 total
includes taxes & fees
Sep 13 - Sep 14
DUNE Fairfield Beach

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is ¥55,153
¥63,426 total
includes taxes & fees
Sep 1 - Sep 2
Guesthouse at Norwalk Inn

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (168 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ¥24,082
¥27,694 total
includes taxes & fees
Aug 30 - Aug 31
Stamford Suites

4. 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 ¥55,561
¥154,162 total
includes taxes & fees
Sep 21 - Sep 22
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

5. 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 ¥48,158
¥73,063 total
includes taxes & fees
Sep 1 - Sep 2
Rustic Cabin in Fishkill!

6. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (17 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is ¥22,288
¥36,934 total
includes taxes & fees
Sep 2 - Sep 3
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

7. 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, (19 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ¥37,969
¥70,651 total
includes taxes & fees
Sep 8 - Sep 9
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

8. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is ¥55,585
¥123,526 total
includes taxes & fees
Sep 27 - Sep 28
Renovated Retreat with Heated Pool

9. 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 ¥42,124
¥68,105 total
includes taxes & fees
Sep 9 - Sep 10
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

10. 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 ¥95,361
¥166,495 total
includes taxes & fees
Sep 1 - Sep 2
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

11. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is ¥158,992
¥238,586 total
includes taxes & fees
Aug 28 - Aug 29
Beechmont - Perfect for Family Retreat!

12. 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, (42 reviews)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is ¥37,412
¥64,834 total
includes taxes & fees
Sep 23 - Sep 24
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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 ¥38,034
¥71,188 total
includes taxes & fees
Sep 15 - Sep 16
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

14. 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 ¥159,200
¥274,120 total
includes taxes & fees
Sep 2 - Sep 3
Private Country Getaway

15. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
United States
Erin D.
The price is ¥167,234
¥266,811 total
includes taxes & fees
Aug 28 - Aug 29
5BR Beach Home | Walk to Cove Beach + Private Yard

16. 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 ¥47,139
¥74,579 total
includes taxes & fees
Sep 9 - Sep 10
Walk to WP Gate + Free Parking!

17. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is ¥77,371
¥154,045 total
includes taxes & fees
Sep 1 - Sep 2
5BR Beach House, Water Views, Game Room, Backyard

18. 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 ¥25,139
¥76,499 total
includes taxes & fees
Sep 2 - Sep 3
Walk-to-Lake Cottage With Grill for Peaceful Fall Days

19. 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 ¥48,142
¥79,632 total
includes taxes & fees
Sep 9 - Sep 10
Fabulous 3bdrm Home w/parking!

20. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
The price is ¥71,672
¥123,594 total
includes taxes & fees
Sep 20 - Sep 21
Awesome Lake Home with tons of fun!
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

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