Guilford, Connecticut

Vacation Rentals in Guilford, Connecticut

Discover 38 vacation rental properties in Guilford. From 1 to 5 bedrooms. Average $416/night. 100% have pools.

38 verified listings Book securely on VRBO Prices updated March 2026

38 properties available

Newly Renovated On Oceanfront Cottage Joshua Cove, Guilford CT

Newly Renovated On Oceanfront Cottage Joshua Cove, Guilford CT

2 beds 3 baths
PoolA/CWiFiBalcony
$677/night
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Quiet 2 bedroom summer haven overlooking beautiful West River

Quiet 2 bedroom summer haven overlooking beautiful West River

2 beds 1 bath
PoolA/CWiFiBalcony
$251/night
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Charming cottage overlooking the Cove

Charming cottage overlooking the Cove

2 beds 1 bath
PoolA/CWiFiBalcony
$215/night
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Cozy Apartment Along Guilford’s Shoreline

Cozy Apartment Along Guilford’s Shoreline

1 bed 1 bath
PoolA/CWiFiBalcony
$203/night
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🌾Brand New Tiny Home! Downtown & Beachy☀️

🌾Brand New Tiny Home! Downtown & Beachy☀️

1 bed 1 bath
PoolA/CWiFiBalcony
$243/night
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Your own Thimble Islands private cottage! (accessible by car via Old Quarry)

Your own Thimble Islands private cottage! (accessible by car via Old Quarry)

1 bed 1 bath
PoolA/CWiFiBalcony
$900/night
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Enjoy a taste of New England in Historic Guilford Ct

Enjoy a taste of New England in Historic Guilford Ct

2 beds 1 bath
PoolA/CWiFiBalcony
$291/night
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Guilford home -self check in, off-street parking

Guilford home -self check in, off-street parking

2 beds 1 bath
PoolA/CWiFiBalcony
$215/night
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Mid-Century Shoreline Cottage; a Birder's Paradise

Mid-Century Shoreline Cottage; a Birder's Paradise

3 beds 1 bath
PoolA/CWiFiBalcony
$386/night
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Rivers Edge Unique Newly Renovated River Spa Free-Standing Air Jet Tub retreat

Rivers Edge Unique Newly Renovated River Spa Free-Standing Air Jet Tub retreat

4 beds 2 baths
PoolA/CWiFiBalcony
$584/night
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STONE GARDEN GETAWAY 🌸Families☀️Reunions🌸Dogs🐶

STONE GARDEN GETAWAY 🌸Families☀️Reunions🌸Dogs🐶

4 beds 2 baths
PoolA/CWiFiBalcony
$504/night
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Simply Beautiful Beach Cottage, 8 min from Guilford Green

Simply Beautiful Beach Cottage, 8 min from Guilford Green

2 beds 1 bath
PoolA/CWiFiBalcony
$265/night
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Newly renovated w/ Brand new kitchen and updated living room with more windows!

Newly renovated w/ Brand new kitchen and updated living room with more windows!

4 beds 2 baths
PoolA/CWiFiBalcony
$474/night
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Great location in historic small shoreline town

Great location in historic small shoreline town

2 beds 1 bath
PoolA/CWiFiBalcony
$211/night
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Great apartment in two family house!

Great apartment in two family house!

1 bed 1 bath
PoolA/CWiFiBalcony
$183/night
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Charming Guilford Cottage - Coastal Views, Peaceful Retreat, Family Memories

Charming Guilford Cottage - Coastal Views, Peaceful Retreat, Family Memories

2 beds 1 bath
PoolA/CWiFiBalcony
$291/night
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Seaside Serenity: Relaxation by Jacob's Beach

Seaside Serenity: Relaxation by Jacob's Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$357/night
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Awesome Views of Long Island Sound! Relax, swim, walk and feel the sea breezes!

Awesome Views of Long Island Sound! Relax, swim, walk and feel the sea breezes!

2 beds 1 bath
PoolA/CWiFiBalcony
$376/night
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1930s Waterfront Cottage on Tuttle's Point

1930s Waterfront Cottage on Tuttle's Point

5 beds 2 baths
PoolA/CWiFiBalcony
$419/night
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🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass

🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass

4 beds 2 baths
PoolA/CWiFiBalcony
$377/night
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Coast and Country Private Estate

Coast and Country Private Estate

3 beds 3 baths
PoolA/CWiFiBalcony
$518/night
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Guilford Carriage House at Granite Lodge!

Guilford Carriage House at Granite Lodge!

1 bed 1 bath
PoolA/CWiFiBalcony
$277/night
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Gorgeous Connecticut BeachHouse ~

Gorgeous Connecticut BeachHouse ~

2 beds 2 baths
PoolA/CWiFiBalcony
$701/night
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Great home walkable to everything! Hydrangea Heaven!

Great home walkable to everything! Hydrangea Heaven!

4 beds 2 baths
PoolA/CWiFiBalcony
$626/night
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Beautiful Long Island Sound Direct Waterfront Cottage, private beach.

Beautiful Long Island Sound Direct Waterfront Cottage, private beach.

2 beds 1 bath
PoolA/CWiFiBalcony
Price on request
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A TREETOPS Retreat! Upscale, Artsy 5 bedroom that sleeps 9-11, With POOL

A TREETOPS Retreat! Upscale, Artsy 5 bedroom that sleeps 9-11, With POOL

5 beds 2 baths
PoolA/CWiFiBalcony
$467/night
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Wonderful apartment ! Great location ! 2 blocks to restaurants and stores

Wonderful apartment ! Great location ! 2 blocks to restaurants and stores

1 bed 1 bath
PoolA/CWiFiBalcony
$171/night
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Lakefront Cottage

Lakefront Cottage

1 bed 1 bath
PoolA/CWiFiBalcony
$177/night
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Charming Beach House 2 BR, 1.5 BTH with waterfront ocean views.

Charming Beach House 2 BR, 1.5 BTH with waterfront ocean views.

2 beds 1 bath
PoolA/CWiFiBalcony
$298/night
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Lakefront Cottage 🕊 quiet

Lakefront Cottage 🕊 quiet

1 bed 2 baths
PoolA/CWiFiBalcony
$149/night
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Cedar Grove Cottage with elevated, stunning views of LI Sound

Cedar Grove Cottage with elevated, stunning views of LI Sound

3 beds 2 baths
PoolA/CWiFiBalcony
$476/night
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Charming cottage by the sea

Charming cottage by the sea

2 beds 2 baths
PoolA/CWiFiBalcony
$351/night
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Waterfront villa on charming bay, minutes to Guilford green, bike & hike nearby

Waterfront villa on charming bay, minutes to Guilford green, bike & hike nearby

3 beds 1 bath
PoolA/CWiFiBalcony
$400/night
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Secluded newly renovated mansion on private road

Secluded newly renovated mansion on private road

4 beds 3 baths
PoolA/CWiFiBalcony
$601/night
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Private luxury waterfront home

Private luxury waterfront home

5 beds 3 baths
PoolA/CWiFiBalcony
$1,702/night
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1780 Historical House on the Shoreline Close to Beaches

1780 Historical House on the Shoreline Close to Beaches

4 beds 1 bath
PoolA/CWiFiBalcony
$500/night
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Private pool, fire pit, hummingbirds in comfortable colonial style private home.

Private pool, fire pit, hummingbirds in comfortable colonial style private home.

4 beds 2 baths
PoolA/CWiFiBalcony
$351/night
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Spacious home in charming shoreline town

Spacious home in charming shoreline town

3 beds 3 baths
PoolA/CWiFiBalcony
$201/night
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