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Litchfield Holiday Rentals

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49 rentals in Litchfield.
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Litchfield Hills Hideaway, holiday rental in Litchfield

Litchfield Hills Hideaway

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Expansive Countryside House, 7 Serene Acres with Pond & Woods, holiday rental in Litchfield

Expansive Countryside House, 7 Serene Acres with Pond & Woods

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Cape in the Litchfield Hills, holiday rental in Litchfield

Cozy Cape in the Litchfield Hills

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Litchfield House w/ Fenced-In Yard & Fire Pit, holiday rental in Litchfield

Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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*New* 2020 Private Modern Farmhouse in Connecticut close to center of Litchfield, holiday rental in Litchfield

*New* 2020 Private Modern Farmhouse in Connecticut close to center of Litchfield

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - Meadow Ridge Farm  Meadow, holiday rental in Litchfield

Tentrr Signature Site - Meadow Ridge Farm Meadow

1 bedroom
1 bathroom
Sleeps 14
Match: Sleeps
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Tentrr Signature Site - Meadow Ridge Farm Woods, holiday rental in Litchfield

Tentrr Signature Site - Meadow Ridge Farm Woods

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Quaint Quiet Serene !!, holiday rental in Litchfield

Quaint Quiet Serene !!

1 bedroom
0 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated 18th Century Cottage On 4 Acres, holiday rental in Litchfield

Newly Renovated 18th Century Cottage On 4 Acres

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., holiday rental in Litchfield

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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TRANQUIL private home with garden OASIS and heated POOL, holiday rental in Litchfield

TRANQUIL private home with garden OASIS and heated POOL

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious family home tucked away in a rural, friendly, lake community!, holiday rental in Litchfield

Spacious family home tucked away in a rural, friendly, lake community!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Short Term Vacation Rental in Kent, holiday rental in Litchfield

Spectacular Short Term Vacation Rental in Kent

3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Historic Warren/Kent Home, holiday rental in Litchfield

Historic Warren/Kent Home

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

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

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Annex/Former Artist Studo, holiday rental in Litchfield

Private Annex/Former Artist Studo

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views, holiday rental in Litchfield

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

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Quaint cottage located directly on Long Meadow Pond, holiday rental in Litchfield

Quaint cottage located directly on Long Meadow Pond

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath), holiday rental in Litchfield

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Warren country retreat, holiday rental in Litchfield

Warren country retreat

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

Waterfront House on Lake Waramaug!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway, holiday rental in Litchfield

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

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Direct Waterfront with Private Beach - Entire Home, holiday rental in Litchfield

Direct Waterfront with Private Beach - Entire Home

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakeridge Litchfield Resort Townhome  Pool  Tennis  Skiing, holiday rental in Litchfield

Lakeridge Litchfield Resort Townhome Pool Tennis Skiing

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Kent Getaway With Views, Pond & Pool, holiday rental in Litchfield

Private Kent Getaway With Views, Pond & Pool

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

SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming country home in Roxbury, holiday rental in Litchfield

Charming country home in Roxbury

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

Mabels Hollow Farm, En suite bedroom farm stay,

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Lake House on the Cleanest Lake in CT, holiday rental in Litchfield

Lake House on the Cleanest Lake in CT

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Prana Residence - Spa, holiday rental in Litchfield

Prana Residence - Spa

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Country Estate newly renovated that sleeps 16!, holiday rental in Litchfield

Country Estate newly renovated that sleeps 16!

5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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NEW! Woodland Retreat w/ Pool & Near Wineries!, holiday rental in Litchfield

NEW! Woodland Retreat w/ Pool & Near Wineries!

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quiet Country Contemporary Home – Ideal Respite From The City, holiday rental in Litchfield

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 Litchfield

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake House  - Direct Waterfront, Immaculate; charming all 4 seasons, holiday rental in Litchfield

Lake House - Direct Waterfront, Immaculate; charming all 4 seasons

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dainty New Preston Cottage w/ Dock & Lake Views!, holiday rental in Litchfield

Dainty New Preston Cottage w/ Dock & Lake Views!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Kent Victorian Room 1, holiday rental in Litchfield

Kent Victorian Room 1

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

Kent Victorian Room 4

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kent Victorian Room 5, holiday rental in Litchfield

Kent Victorian Room 5

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

Kent Victorian Room 3

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

Kent Victorian Room 2

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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4 Room Apartment, holiday rental in Litchfield

4 Room Apartment

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Goshen House w/ Deck, Backyard & Views, holiday rental in Litchfield

Modern Goshen House w/ Deck, Backyard & Views

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

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 Litchfield

Direct Lakefront, Bantam Lake, Private Deer Island

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ultimate Staycation Home in a Serene Setting, holiday rental in Litchfield

Ultimate Staycation Home in a Serene Setting

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Flat - Pals - 2 Bedrooms, 1 Bathrooms, Lift, Urbanizacion, holiday rental in Litchfield

Flat - Pals - 2 Bedrooms, 1 Bathrooms, Lift, Urbanizacion

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! 2,438 Sq Ft Washington House - Pets Welcome!, holiday rental in Litchfield

NEW! 2,438 Sq Ft Washington House - Pets Welcome!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Whimsical Cottage in Washington w/ Fire Pit!, holiday rental in Litchfield

NEW! Whimsical Cottage in Washington w/ Fire Pit!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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