Vacation rentals in Sherman, CT

Best Vacation rentals and Airbnb offers in Sherman, CT

Station Inn Pawling

Guest House, Sherman

Station Inn Pawling is a guest house in Sherman, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About Station Inn Pawling

Station Inn Pawling is a guest house in Sherman, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,718.

From$217/night

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Dainty New Preston Cottage w/ Dock & Lake Views!

Holiday Home, Sherman

Dainty New Preston Cottage w/ Dock & Lake Views! is a holiday home in Sherman, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Dainty New Preston Cottage w/ Dock & Lake Views!

Dainty New Preston Cottage w/ Dock & Lake Views! is a holiday home in Sherman, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,533.

From$259/night

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Artistic barn: wood burning hottub, sauna and pizza oven

Holiday Home, Sherman

Artistic barn: wood burning hottub, sauna and pizza oven is a holiday home in Sherman, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Artistic barn: wood burning hottub, sauna and pizza oven

Artistic barn: wood burning hottub, sauna and pizza oven is a holiday home in Sherman, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,862.

From$266/night

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Barn Apartment Hideaway

Apartment, Sherman

Barn Apartment Hideaway is a apartment in Sherman, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Barn Apartment Hideaway

Barn Apartment Hideaway is a apartment in Sherman, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,864.

From$266/night

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Browse Vacation Rentals with a Pool in Sherman, CT

Add a pool to the search when you want an easy place to cool off between outings.

Charming 2-bedroom villa in serene Holmes with AC, WiFi

Villa, Sherman

Charming 2-bedroom villa in serene Holmes with AC, WiFi is a villa in Sherman, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Charming 2-bedroom villa in serene Holmes with AC, WiFi

Charming 2-bedroom villa in serene Holmes with AC, WiFi is a villa in Sherman, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,825.

From$689/night

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Fabulous 4 Season Resort Home on the Ten Mile River

Holiday Home, Sherman

Fabulous 4 Season Resort Home on the Ten Mile River is a holiday home in Sherman, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Fabulous 4 Season Resort Home on the Ten Mile River

Fabulous 4 Season Resort Home on the Ten Mile River is a holiday home in Sherman, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,783.

From$826/night

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BEST Town, Restaurants, 1.5 Hrs NYC! PoshPadsCT HEATED SPA-POOL, Bike, Hike, Ski

Holiday Home, Sherman

BEST Town, Restaurants, 1.5 Hrs NYC! PoshPadsCT HEATED SPA-POOL, Bike, Hike, Ski is a holiday home in Sherman, with pet-friendly space and pool access. This stay gives travelers a…

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About BEST Town, Restaurants, 1.5 Hrs NYC! PoshPadsCT HEATED SPA-POOL, Bike, Hike, Ski

BEST Town, Restaurants, 1.5 Hrs NYC! PoshPadsCT HEATED SPA-POOL, Bike, Hike, Ski is a holiday home in Sherman, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,117.

From$1,017/night

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Private hidden gem walking distance to town, restaurants, and shopping!

Holiday Home, Sherman

Private hidden gem walking distance to town, restaurants, and shopping! is a holiday home in Sherman, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Private hidden gem walking distance to town, restaurants, and shopping!

Private hidden gem walking distance to town, restaurants, and shopping! is a holiday home in Sherman, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,254.

From$1,036/night

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Best Sherman, CT vacation rentals with parking

Find vacation rentals that make arriving by car easier.

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

Holiday Home, Sherman

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley is a holiday home in Sherman, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley is a holiday home in Sherman, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,665.

From$381/night

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Roxbury Cabin Retreat

Cabin, Sherman

Roxbury Cabin Retreat is a cabin in Sherman, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Roxbury Cabin Retreat

Roxbury Cabin Retreat is a cabin in Sherman, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,835.

From$405/night

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Reunions at Candlewood Lake

Holiday Home, Sherman

Reunions at Candlewood Lake is a holiday home in Sherman, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Reunions at Candlewood Lake

Reunions at Candlewood Lake is a holiday home in Sherman, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,062.

From$580/night

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NYC-Area Escape • Game Room • Firepit • Chef's Kitchen • Near Boarding Schools

Holiday Home, Sherman

NYC-Area Escape · Game Room · Firepit · Chef's Kitchen · Near Boarding Schools is a holiday home in Sherman, with parking and kitchen access. This stay gives travelers a comfortable base…

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About NYC-Area Escape • Game Room • Firepit • Chef's Kitchen • Near Boarding Schools

NYC-Area Escape · Game Room · Firepit · Chef's Kitchen · Near Boarding Schools is a holiday home in Sherman, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,213.

From$602/night

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Best Pet-Friendly Vacation Rentals in Sherman, CT

Bring your pet along with stays that welcome four-legged travelers.

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Holiday Home, Sherman

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC is a holiday home in Sherman, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for…

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About Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC is a holiday home in Sherman, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, gym, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,921.

From$274/night

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Litchfield County Getaway

Holiday Home, Sherman

Litchfield County Getaway is a holiday home in Sherman, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Litchfield County Getaway

Litchfield County Getaway is a holiday home in Sherman, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,358.

From$337/night

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Direct Water Front Home, Private Boat Dock, Kayaks

Holiday Home, Sherman

Direct Water Front Home, Private Boat Dock, Kayaks is a holiday home in Sherman, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Direct Water Front Home, Private Boat Dock, Kayaks

Direct Water Front Home, Private Boat Dock, Kayaks is a holiday home in Sherman, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,704.

From$815/night

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Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Chalet, Sherman

Enchanting Lake front chalet with backyard and fire pit. Dog friendly. is a chalet in Sherman, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly. is a chalet in Sherman, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,643.

From$378/night

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Best Sherman, CT vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Charming country home in Roxbury

Holiday Home, Sherman

Charming country home in Roxbury is a holiday home in Sherman, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Charming country home in Roxbury

Charming country home in Roxbury is a holiday home in Sherman, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,506.

From$501/night

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Connecticut Getaway Extended Stay

Holiday Home, Sherman

Connecticut Getaway Extended Stay is a holiday home in Sherman, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Connecticut Getaway Extended Stay

Connecticut Getaway Extended Stay is a holiday home in Sherman, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,056.

From$579/night

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Candlewood Lake Retreat Extended Stay

Holiday Home, Sherman

Candlewood Lake Retreat Extended Stay is a holiday home in Sherman, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Candlewood Lake Retreat Extended Stay

Candlewood Lake Retreat Extended Stay is a holiday home in Sherman, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,062.

From$580/night

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Lakefront Oasis - Kayaks - Hot Tub - Fire Pit

Holiday Home, Sherman

Lakefront Oasis - Kayaks - Hot Tub - Fire Pit is a holiday home in Sherman, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lakefront Oasis - Kayaks - Hot Tub - Fire Pit

Lakefront Oasis - Kayaks - Hot Tub - Fire Pit is a holiday home in Sherman, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,633.

From$1,090/night

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Our Favorite Family-Friendly Vacation Rentals in Sherman, CT

Plan a trip with stays that give families more room to spread out.

Fabulous 2-bedroom Creekside cottage on the historic Collins Estate.

Cottage, Sherman

Fabulous 2-bedroom Creekside cottage on the historic Collins Estate. is a cottage in Sherman, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Fabulous 2-bedroom Creekside cottage on the historic Collins Estate.

Fabulous 2-bedroom Creekside cottage on the historic Collins Estate. is a cottage in Sherman, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,170.

From$310/night

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Charming Country Cottage w pool and pickleball court

Cottage, Sherman

Charming Country Cottage w pool and pickleball court is a cottage in Sherman, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming Country Cottage w pool and pickleball court

Charming Country Cottage w pool and pickleball court is a cottage in Sherman, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,571.

From$367/night

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One of the Original Summer Cottages on Lake Warmaug

Holiday Home, Sherman

One of the Original Summer Cottages on Lake Warmaug is a holiday home in Sherman, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About One of the Original Summer Cottages on Lake Warmaug

One of the Original Summer Cottages on Lake Warmaug is a holiday home in Sherman, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,337.

From$620/night

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Cozy Candlewood Lake Cabin — Family + Friend Retreat

Holiday Home, Sherman

Cozy Candlewood Lake Cabin — Family + Friend Retreat is a holiday home in Sherman, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy Candlewood Lake Cabin — Family + Friend Retreat

Cozy Candlewood Lake Cabin — Family + Friend Retreat is a holiday home in Sherman, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,914.

From$702/night

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