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35 Houses

14

Lake Cottage with Views and Fireplace

Connecticut / Sherman

Sherman house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$198

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$198

Great rentals within 20 miles that match your search

Distance approx 15.63 km from Sherman

(5) Excellent 

19

Its the Perfect Weekend House just 80min from NYC!

Connecticut / Woodbury

Woodbury house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden

Price per night from

$159

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$159

Distance approx 12.16 km from Sherman

32

Lake House with Indoor Spa, 1 hour from Manhattan

New York / Carmel

Carmel house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$200

Price per night from

$200

Distance approx 6.58 km from Sherman Show on Map

24

Unique New Fairfield House w/ Deck & Lake Views!

Connecticut / New Fairfield

New Fairfield house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$249

Responds fast!
avg. 10 minutes

Price per night from

$249

Distance approx 14.65 km from Sherman

(1) Excellent 

27

Quiet Getaway in Historic Village

Connecticut / Southbury

Southbury house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 3 mi
  • Child Friendly
  • Car not necessary

Price per night from

$158

Price per night from

$158

Distance approx 7.08 km from Sherman

29

Lake House Rental On Your Own Private Lake

New York / Wingdale

Wingdale villa

4 11 4 nights min

  • 4 bedrooms
  • sleeps 11
  • 4 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$621

Price per night from

$621

Distance approx 10.08 km from Sherman

30

South Street 4-BR Cottage with Heated Pool

Connecticut / Washington

Washington house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$690

Price per night from

$690

Distance approx 15.85 km from Sherman

8

Large Private Apartment

New York / Verbank

Verbank apartment

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly

Price per night from

$100

Price per night from

$100

Distance approx 16.23 km from Sherman

24

Prana Residence - Spa

Connecticut / Cornwall Bridge

Cornwall Bridge house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$745

Price per night from

$745

Distance approx 10.36 km from Sherman

24

Lakefront New Preston Cottage w/Dock & Fire Pit!

Connecticut / New Preston

New Preston cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$199

Responds fast!
avg. 9 minutes

Price per night from

$199

Distance approx 8.98 km from Sherman

(9) Very Good 

20

Lake Bliss the Perfect Getaway

New York / Holmes

Holmes house

3 10 1 night min

  • 3 bedrooms
  • sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$250

Price per night from

$250

Distance approx 17.74 km from Sherman

27

Country Estate newly renovated that sleeps 16!

Connecticut / Bethlehem

Bethlehem house

5 16 3 nights min

  • 5 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly

Price per night from

$224

Responds fast!
avg. 20 minutes

Price per night from

$224

Distance approx 14.65 km from Sherman

20

Frank Lloyd Wright Retreat with Outdoor Pool on 8 Secluded Acres

New York / LaGrangeville

LaGrangeville house

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min

Price per night from

$694

Price per night from

$694

Distance approx 18.08 km from Sherman

16

Charming COTTAGE near NYC!

Westchester County / North Salem

North Salem cottage

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$293

Price per night from

$293

Distance approx 19.23 km from Sherman

(1) Excellent 

24

Litchfield House on Half Acre - 1 Mile to Town!

Connecticut / Litchfield

Litchfield house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$211

Responds fast!
avg. 10 minutes

Price per night from

$211

Distance approx 3.8 km from Sherman Show on Map

(4) Excellent 

36

20'x40' inground private pool just for you&house with 4bedrooms

Connecticut / New Milford

New Milford house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
“Wonderful experience!!!” My wife and our two children (10 and 7)spent a wonderful time at this beautiful New Milford retreat. The house was spacious and nicely decorated and we loved the privacy of the place. You couldn't see any neighbors and yet sho
…see more

Price per night from

$284

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$284

Distance approx 14.15 km from Sherman

(1) Excellent 

16

Wits End Farm

Connecticut / Bethlehem

Bethlehem house

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$889

Price per night from

$889

Distance approx 14.57 km from Sherman

12

A Historic Home for Guests and Lawns/Facilities for Gatherings such as Weddings

Connecticut / Southbury

Southbury house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$198

Price per night from

$198

Distance approx 14.15 km from Sherman

(1) Excellent 

14

Wits End Farm B&B

Connecticut / Bethlehem

Bethlehem b and b

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Child Friendly

Price per night from

$794

Price per night from

$794

Distance approx 15.68 km from Sherman

24

Victorian Newtown Apt w/Fire Pit 20 Mi to Jennings

Connecticut / Newtown

Newtown apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Ski
  • Suitable for children age 5+

Price per night from

$139

Responds fast!
avg. 10 minutes

Price per night from

$139

Distance approx 10.41 km from Sherman

8

Kent Victorian Room 3

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$148

Price per night from

$148

Distance approx 10.41 km from Sherman

8

Kent Victorian Room 4

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$110

Price per night from

$110

Distance approx 19.8 km from Sherman

44

1790 Classic Colonial Center Hall home

Connecticut / Sharon

Sharon house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Child Friendly

Price per night from

$497

Price per night from

$497

Distance approx 10.41 km from Sherman

8

Kent Victorian Room 2

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149

Distance approx 9.77 km from Sherman

(1) Excellent 

23

Rhubarb Hill, a Charming 1850's Farmhouse

Connecticut / New Preston

New Preston house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$348

Price per night from

$348

Distance approx 3.79 km from Sherman Show on Map

29

Very private,4bdrm house,20x40inground pool, pool house. Paradise!

Connecticut / New Milford

New Milford house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$348

Price per night from

$348

Distance approx 11.31 km from Sherman

25

Lakefront Warren 'Carriage House' on 25 Acres!

Connecticut / Warren

Warren house

7 14 4 nights min

  • 7 bedrooms
  • sleeps 14
  • 4 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$987

Responds fast!
avg. 14 minutes

Price per night from

$987

Distance approx 10.41 km from Sherman

8

Kent Victorian Room 5

Connecticut / Kent

Kent room

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$158

Price per night from

$158

Distance approx 7.16 km from Sherman

(1) Excellent 

31

Private Lakefront & Pool DeeLuxGlamping. NYC Getaway

New York / Pawling

Pawling camper van

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$156

Price per night from

$156

Distance approx 10.41 km from Sherman

6

Kent Victorian Room 1

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$159

Price per night from

$159

Distance approx 18.7 km from Sherman

4

Exclusive Rental in Beautiful Amenia!

New York / Amenia

Amenia house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$133

Price per night from

$133

Distance approx 14.62 km from Sherman

8

Library Bed Room with Fireplace, Dressing Room and Separate Entry from outside

Connecticut / Southbury

Southbury room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Private garden

Price per night from

$90

Price per night from

$90

Distance approx 4.85 km from Sherman Show on Map

(1)  

32

Must Love Garden and the Sound of Stream

New York / Lanesville

Lanesville house

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$249

Price per night from

$249

Distance approx 10.84 km from Sherman

7

2 Bedroom Suite with Kitchen

Connecticut / Roxbury

Roxbury hotel apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$248

Price per night from

$248

Distance approx 16.02 km from Sherman

20

LAKEFRONT COTTAGE ON PRISTINE LAKE

New York / Carmel

Carmel cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$224

Price per night from

$224