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Kent Holiday Rentals

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50 rentals in Kent.
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Spectacular Short Term Vacation Rental in Kent, holiday rental in Kent

Spectacular Short Term Vacation Rental in Kent

3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Modern cottage on the Housatonic River, holiday rental in Kent

Modern cottage on the Housatonic River

1 bedroom
1 bathroom
Sleeps 2
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Private Kent Getaway With Views, Pond & Pool, holiday rental in Kent

Private Kent Getaway With Views, Pond & Pool

2 bedrooms
2 bathrooms
Sleeps 4
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Kent Victorian Room 5, holiday rental in Kent

Kent Victorian Room 5

2 bedrooms
1 bathroom
Sleeps 3
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Kent Victorian Room 1, holiday rental in Kent

Kent Victorian Room 1

1 bedroom
1 bathroom
Sleeps 2
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Kent Victorian Room 3, holiday rental in Kent

Kent Victorian Room 3

1 bedroom
1 bathroom
Sleeps 2
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Kent Victorian Room 4, holiday rental in Kent

Kent Victorian Room 4

1 bedroom
1 bathroom
Sleeps 2
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Kent Victorian Room 2, holiday rental in Kent

Kent Victorian Room 2

1 bedroom
1 bathroom
Sleeps 2
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Welcome to The Lake: Your Private Paradise Awaits!, holiday rental in Kent

Welcome to The Lake: Your Private Paradise Awaits!

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., holiday rental in Kent

Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Newly Renovated 18th Century Cottage On 4 Acres, holiday rental in Kent

Newly Renovated 18th Century Cottage On 4 Acres

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Peaceful Candlewood  lake/woods retreat., holiday rental in Kent

Peaceful Candlewood lake/woods retreat.

3 bedrooms
2 bathrooms
Sleeps 8
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Stylish and modern house in the quaint town of Millbrook., holiday rental in Kent

Stylish and modern house in the quaint town of Millbrook.

3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video, holiday rental in Kent

Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video

4 bedrooms
4 bathrooms
Sleeps 8
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Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views, holiday rental in Kent

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

3 bedrooms
4 bathrooms
Sleeps 9
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Prime Direct Waterfront On Candlewood Lake, Private Dock, Cozy Lake House, holiday rental in Kent

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

3 bedrooms
2 bathrooms
Sleeps 6
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House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres, holiday rental in Kent

House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres

3 bedrooms
1 bathroom
Sleeps 8
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Historic Warren/Kent Home, holiday rental in Kent

Historic Warren/Kent Home

3 bedrooms
3 bathrooms
Sleeps 6
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Direct Water Front Home, holiday rental in Kent

Direct Water Front Home

3 bedrooms
2 bathrooms
Sleeps 6
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Expansive Countryside House, 7 Serene Acres with Pond & Woods, holiday rental in Kent

Expansive Countryside House, 7 Serene Acres with Pond & Woods

3 bedrooms
2 bathrooms
Sleeps 6
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TREEMENDOUS VIEWS COTTAGE, holiday rental in Kent

TREEMENDOUS VIEWS COTTAGE

4 bedrooms
2 bathrooms
Sleeps 8
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Mountainview - Vacation Rental in Sharon, CT, holiday rental in Kent

Mountainview - Vacation Rental in Sharon, CT

3 bedrooms
2 bathrooms
Sleeps 8
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Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway, holiday rental in Kent

Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway

3 bedrooms
2 bathrooms
Sleeps 7
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Secluded country cabin upstate New York, near  metro north train, holiday rental in Kent

Secluded country cabin upstate New York, near metro north train

1 bedroom
1 bathroom
Sleeps 6
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Private Annex/Former Artist Studo, holiday rental in Kent

Private Annex/Former Artist Studo

2 bedrooms
1 bathroom
Sleeps 4
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Warren country retreat, holiday rental in Kent

Warren country retreat

3 bedrooms
2 bathrooms
Sleeps 6
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The Hilltop - Stunning, holiday rental in Kent

The Hilltop - Stunning

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront House on Lake Waramaug!, holiday rental in Kent

Waterfront House on Lake Waramaug!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU, holiday rental in Kent

SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Immaculate 1780 Millbrook Classic, holiday rental in Kent

Immaculate 1780 Millbrook Classic

5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Serene, Peaceful Get-Away (Log Cabin by the Lake), holiday rental in Kent

Serene, Peaceful Get-Away (Log Cabin by the Lake)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rustic Country Beach Cottage Candlewood Lake, holiday rental in Kent

Rustic Country Beach Cottage Candlewood Lake

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Mabels Hollow Farm, En suite bedroom farm stay,, holiday rental in Kent

Mabels Hollow Farm, En suite bedroom farm stay,

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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100% WASHINGTON!PoshPadsCT 'PLUMB HILL' 5BR, Pool, Bikes, BBQ Near Mayflower Inn, holiday rental in Kent

100% WASHINGTON!PoshPadsCT 'PLUMB HILL' 5BR, Pool, Bikes, BBQ Near Mayflower Inn

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Prana Residence - Spa, holiday rental in Kent

Prana Residence - Spa

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Millbrook Country Dream! Tennis/Swim/Play, holiday rental in Kent

Millbrook Country Dream! Tennis/Swim/Play

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful mountaintop getaway for peace and quiet, holiday rental in Kent

Beautiful mountaintop getaway for peace and quiet

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake House Rental On Your Own Private Lake, holiday rental in Kent

Lake House Rental On Your Own Private Lake

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Quiet Country Contemporary Home – Ideal Respite From The City, holiday rental in Kent

Quiet Country Contemporary Home – Ideal Respite From The City

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, holiday rental in Kent

100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Exclusive Rental in Beautiful Amenia!, holiday rental in Kent

Exclusive Rental in Beautiful Amenia!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dainty New Preston Cottage w/ Dock & Lake Views!, holiday rental in Kent

Dainty New Preston Cottage w/ Dock & Lake Views!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1790 Classic Colonial Center Hall home, holiday rental in Kent

1790 Classic Colonial Center Hall home

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Sherman Home w/Lakefront Deck & Swimming Dock, holiday rental in Kent

Sherman Home w/Lakefront Deck & Swimming Dock

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serene haven in the country, holiday rental in Kent

Serene haven in the country

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Direct Lakefront, Bantam Lake, Private Deer Island, holiday rental in Kent

Direct Lakefront, Bantam Lake, Private Deer Island

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Listing!  Stunning Country Home 90 Minutes from NYC, holiday rental in Kent

New Listing! Stunning Country Home 90 Minutes from NYC

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming country home in Roxbury, holiday rental in Kent

Charming country home in Roxbury

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Family Getaway w/ Fireplace in Sherman on 4 Acres!, holiday rental in Kent

Family Getaway w/ Fireplace in Sherman on 4 Acres!

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath), holiday rental in Kent

Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Kent


Yes, here are some popular holiday rentals in Kent that have internet access:See all holiday rentals in Kent on Tripadvisor