Top 50 Kent Vacation Rentals

Houses (152)
Cottages (37)
Farmhouses (15)
Golf rental (169)
Ski rental (77)
Lake view (67)

Discover popular destinations in and around Kent

South Kent

8 vacation rentals

Macedonia Brook State Park

270 vacation rentals

Kent Falls State Park

Eric Sloane Museum and Kent Iron Furnace

257 vacation rentals

Morrison Gallery

256 vacation rentals

Macedonia Brook State Park

270 vacation rentals

Kent Falls State Park

Eric Sloane Museum and Kent Iron Furnace

257 vacation rentals

Morrison Gallery

256 vacation rentals

Explore a selection of Kent vacation rentals

Charming Country Cottage
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$212 avg/night
2 beds
2 Bathrooms
Guests 4
39 reviews
In town, walk to everything, close to Kent, South Kent and...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$200 avg/night
2 beds
1 Bathroom
Guests 4
11 reviews
Berkshire Place - Spectacular View
Guests7
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$280 avg/night
3 beds
2 Bathrooms
Guests 7
2 reviews
Spectacular Short Term Vacation Rental in Kent
Guests14
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$350 avg/night
3 beds
2 Bathrooms
Guests 14
37 reviews
Stunning 1740's white country cottage available throughout the...
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$300 avg/night
3 beds
2 Bathrooms
Guests 6
2 reviews
Historic Warren/Kent Home
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$322 avg/night
3 beds
3 Bathrooms
Guests 6
1 reviews
Enjoy the Hamptons of New England in a Renovated Barn,
Guests11
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$429 avg/night
5 beds
4 Bathrooms
Guests 11
2 reviews
Secluded Country Retreat
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$375 avg/night
3 beds
2 Bathrooms
Guests 6
1 reviews
Kent-Spectacular Panoramic View of Litchfield Hills- Private Lake...
Guests12
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$730 avg/night
4 beds
4 Bathrooms
Guests 12
1 reviews
weekly/monthly/seasonal/yearly Rates- Long Term Option
Guests4
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$107 avg/night
2 beds
2 Bathrooms
Guests 4
Chalet Home at Candlewood Lake, Beach, Owner Managed.
Guests6
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$110 avg/night
2 beds
1 Bathroom
Guests 6
51 reviews
Charming Country House Overlooking Candlewood Lake, Beach
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$186 avg/night
3 beds
2 Bathrooms
Guests 6
30 reviews
CANDLE WOOD ISLE LAKE HOUSE EARLY FALL GETAWAY LOW RATES
Guests6
Bedrooms4
Bathroom1
Wonderful 4.8 / 5
$118 avg/night
4 beds
1 Bathroom
Guests 6
5 reviews
Beautiful Candlewood Isle Cottage With Spectacular Lake Views.
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$227 avg/night
2 beds
1 Bathroom
Guests 5
13 reviews
Spacious Restored Barn on 700 acre Estate with Magnficent Views
Guests12
Bedrooms6
Bathrooms6
Wonderful 4.5 / 5
$500 avg/night
6 beds
6 Bathrooms
Guests 12
16 reviews
Log Cabin On A Lake With Private Dock
Guests6
Bedrooms3
Bathroom1
Wonderful 5 / 5
$264 avg/night
3 beds
1 Bathroom
Guests 6
47 reviews
Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views
Guests9
Bedrooms3
Bathrooms2
Wonderful 4.6 / 5
$300 avg/night
3 beds
2 Bathrooms
Guests 9
16 reviews
Spectacular views, secluded, three bedroom house, close to...
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$350 avg/night
3 beds
2 Bathrooms
Guests 6
6 reviews
Kozy Direct Waterfront cottage, One Of A Kind Private Lake Loc, 2...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$292 avg/night
2 beds
1 Bathroom
Guests 4
35 reviews
Beautiful Cottage and Waterfront Access
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$221 avg/night
2 beds
2 Bathrooms
Guests 4
9 reviews
1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
Guests9
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$250 avg/night
5 beds
4 Bathrooms
Guests 9
8 reviews
Beautiful Large Estate In The Country, Nearby Skiing, Short Or...
Guests22
Bedrooms6
Bathrooms4
Wonderful 4.9 / 5
$909 avg/night
6 beds
4 Bathrooms
Guests 22
18 reviews
Idyllic Family Retreat on Candlewood Lake Beach
Guests12
Bedrooms5
Bathrooms3
Wonderful 4.8 / 5
$267 avg/night
5 beds
3 Bathrooms
Guests 12
6 reviews
Charming Lakefront Cabin And Guest Cottage With Spectacular View
Guests10
Bedrooms5
Bathrooms2
Wonderful 5 / 5
$500 avg/night
5 beds
2 Bathrooms
Guests 10
7 reviews
The Beehive Cottage in Cornwall Bridge MONTHLY RENTAL
Guests9
Bedrooms4
Bathroom1
Wonderful 5 / 5
$70 avg/night
4 beds
1 Bathroom
Guests 9
1 reviews
1900 Pawling Village Home By Darryls House,Thunder Ridge,Trinity...
Guests6
Bedrooms3
Bathroom1
Wonderful 4.8 / 5
$183 avg/night
3 beds
1 Bathroom
Guests 6
22 reviews
Modern Dwell-published home - available throughout the year
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$164 avg/night
3 beds
2 Bathrooms
Guests 6
12 reviews
Escape to the lake. Your own lake. Period.
Guests11
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$626 avg/night
4 beds
3 Bathrooms
Guests 11
29 reviews
Rustic Streamside Cabin, Quiet Escape near Fly fishing, hiking...
Guests3
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$107 avg/night
1 bed
1 Bathroom
Guests 3
8 reviews
Newly Renovated 18th Century Cottage On 4 Acres
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$183 avg/night
2 beds
2 Bathrooms
Guests 5
2 reviews
Tyler Lake Cottage. Pet Friendly, Close To Litchfield For Fine...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.4 / 5
$150 avg/night
2 beds
1 Bathroom
Guests 4
5 reviews
Lakefront House---Sleeps 10--1 Hour from NYC...
Guests10
Bedrooms5
Bathrooms3
Wonderful 4.8 / 5
$429 avg/night
5 beds
3 Bathrooms
Guests 10
26 reviews
90 miles from NYC, Millbrook is beautiful horse farm country...
Guests8
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$500 avg/night
4 beds
2 Bathrooms
Guests 8
17 reviews
Lakeville/Salisbury retreat with lake access - Steps from...
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$500 avg/night
3 beds
3 Bathrooms
Guests 8
3 reviews
Prime Direct Waterfront On Candlewood Lake, Private Dock, Cozy...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$220 avg/night
3 beds
2 Bathrooms
Guests 6
10 reviews
Expansive Property with Beautiful Waterfront Setting in Sherman, CT
Guests10
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$500 avg/night
4 beds
3 Bathrooms
Guests 10
6 reviews
Peaceful, Secluded Brookside Home in Litchfield County
Guests6
Bedrooms3
Bathroom1
Wonderful 4.9 / 5
$173 avg/night
3 beds
1 Bathroom
Guests 6
14 reviews
Peaceful, Secluded Brookside Home in Litchfield County
Guests8
Bedrooms3
Bathroom1
Wonderful 4.9 / 5
$167 avg/night
3 beds
1 Bathroom
Guests 8
14 reviews
Breathe, Recharge, Create! Private Property Spectacular Views In...
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$393 avg/night
3 beds
3 Bathrooms
Guests 6
5 reviews
Direct Candlewood Lake Front in a sought after location.
Guests9
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$529 avg/night
4 beds
3 Bathrooms
Guests 9
16 reviews
Scenic Lakefront Retreat
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$283 avg/night
3 beds
2 Bathrooms
Guests 8
14 reviews
Private Romantic Retreat, Stunning Hudson Valley Views over Cows...
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$156 avg/night
2 beds
1 Bathroom
Guests 4
8 reviews
Candlewood Lake - Sprawling Waterfront Getaway. Sleeps 10
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.9 / 5
$500 avg/night
4 beds
2 Bathrooms
Guests 10
7 reviews
House on Lake Waramaug
Guests7
Bedrooms3
Bathrooms2
Wonderful 4.3 / 5
$280 avg/night
3 beds
2 Bathrooms
Guests 7
7 reviews
Furnished 4 Bedroom Home In Center Of Lakeville 200 Feet From Town...
Guests10
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$236 avg/night
4 beds
2 Bathrooms
Guests 10
15 reviews
Adorable 2 Bedroom Lake Cottage- Very Quiet and Private!
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$160 avg/night
2 beds
1 Bathroom
Guests 5
19 reviews
Lakefront Escape with Gorgeous Views a Short Trip from New York...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$275 avg/night
3 beds
2 Bathrooms
Guests 6
17 reviews
Clinton Corners Hideaway: Handcrafted Home On 2 Acres In Bucolic...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$214 avg/night
2 beds
2 Bathrooms
Guests 6
45 reviews
Private Country Retreat in Lovely Lakeville CT
Guests10
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$295 avg/night
3 beds
2 Bathrooms
Guests 10
3 reviews
Complete Privacy, Tranquil Waterfront in the Litchfield Hills
Guests8
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$371 avg/night
4 beds
3 Bathrooms
Guests 8
38 reviews

Kent, CT, USA Vacation Rentals

Discover popular destinations in and around Kent

Charming Country Cottage

In town, walk to everything, close to Kent, South Kent and...

Berkshire Place - Spectacular View

Spectacular Short Term Vacation Rental in Kent

Stunning 1740's white country cottage available throughout the...

Historic Warren/Kent Home

Enjoy the Hamptons of New England in a Renovated Barn,

Secluded Country Retreat

Kent-Spectacular Panoramic View of Litchfield Hills- Private Lake...

weekly/monthly/seasonal/yearly Rates- Long Term Option

Chalet Home at Candlewood Lake, Beach, Owner Managed.

Charming Country House Overlooking Candlewood Lake, Beach

CANDLE WOOD ISLE LAKE HOUSE EARLY FALL GETAWAY LOW RATES

Beautiful Candlewood Isle Cottage With Spectacular Lake Views.

Spacious Restored Barn on 700 acre Estate with Magnficent Views

Log Cabin On A Lake With Private Dock

Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views

Spectacular views, secluded, three bedroom house, close to...

Kozy Direct Waterfront cottage, One Of A Kind Private Lake Loc, 2...

Beautiful Cottage and Waterfront Access

1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9

Beautiful Large Estate In The Country, Nearby Skiing, Short Or...

Idyllic Family Retreat on Candlewood Lake Beach

Charming Lakefront Cabin And Guest Cottage With Spectacular View

The Beehive Cottage in Cornwall Bridge MONTHLY RENTAL

1900 Pawling Village Home By Darryls House,Thunder Ridge,Trinity...

Modern Dwell-published home - available throughout the year

Escape to the lake. Your own lake. Period.

Rustic Streamside Cabin, Quiet Escape near Fly fishing, hiking...

Newly Renovated 18th Century Cottage On 4 Acres

Tyler Lake Cottage. Pet Friendly, Close To Litchfield For Fine...

Lakefront House---Sleeps 10--1 Hour from NYC...

90 miles from NYC, Millbrook is beautiful horse farm country...

Lakeville/Salisbury retreat with lake access - Steps from...

Prime Direct Waterfront On Candlewood Lake, Private Dock, Cozy...

Expansive Property with Beautiful Waterfront Setting in Sherman, CT

Peaceful, Secluded Brookside Home in Litchfield County

Peaceful, Secluded Brookside Home in Litchfield County

Breathe, Recharge, Create! Private Property Spectacular Views In...

Direct Candlewood Lake Front in a sought after location.

Scenic Lakefront Retreat

Private Romantic Retreat, Stunning Hudson Valley Views over Cows...

Candlewood Lake - Sprawling Waterfront Getaway. Sleeps 10

House on Lake Waramaug

Furnished 4 Bedroom Home In Center Of Lakeville 200 Feet From Town...

Adorable 2 Bedroom Lake Cottage- Very Quiet and Private!

Lakefront Escape with Gorgeous Views a Short Trip from New York...

Clinton Corners Hideaway: Handcrafted Home On 2 Acres In Bucolic...

Private Country Retreat in Lovely Lakeville CT

Complete Privacy, Tranquil Waterfront in the Litchfield Hills