Vacation rentals in Pawling, NY

Best vacation rentals and Airbnb offers in Pawling, NY

10 ★ 108 reviews

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Holiday Home, Pawling

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. is a holiday home in Pawling, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. is a holiday home in Pawling, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,985.

From$284/night

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10 ★ 37 reviews

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Apartment, Pawling

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake is a apartment in Pawling, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake is a apartment in Pawling, 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, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,281.

From$326/night

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10 ★ 19 reviews

Beautiful lake view home on Whaley Lake in Holmes, NY.

Holiday Home, Pawling

Beautiful lake view home on Whaley Lake in Holmes, NY. is a holiday home in Pawling, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beautiful lake view home on Whaley Lake in Holmes, NY.

Beautiful lake view home on Whaley Lake in Holmes, NY. is a holiday home in Pawling, 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, kitchen, with kitchen, washer, and dryer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,339.

From$620/night

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10 ★ 9 reviews

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

Cottage, Pawling

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC is a cottage in Pawling, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC is a cottage in Pawling, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,340.

From$477/night

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Family-friendly vacation rentals in Pawling, NY

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

10 ★ 127 reviews

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Holiday Home, Pawling

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing! is a holiday home in Pawling, with pet-friendly space and room for a group. This stay gives travelers a…

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About Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing! is a holiday home in Pawling, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,685.

From$812/night

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10 ★ 1 reviews

Cozy Lake Cottage with Hot Tub, Views, Kayaks

Cottage, Pawling

Cozy Lake Cottage with Hot Tub, Views, Kayaks is a cottage in Pawling, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Lake Cottage with Hot Tub, Views, Kayaks

Cozy Lake Cottage with Hot Tub, Views, Kayaks is a cottage in Pawling, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,718.

From$388/night

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10 ★ 1 reviews

Lake View Cottage in Candlewood Lake Community

Holiday Home, Pawling

Lake View Cottage in Candlewood Lake Community is a holiday home in Pawling, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lake View Cottage in Candlewood Lake Community

Lake View Cottage in Candlewood Lake Community is a holiday home in Pawling, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,247.

From$464/night

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10 ★ 1 reviews

The Little Lake Cabin with hot tub

Cabin, Pawling

The Little Lake Cabin with hot tub is a cabin in Pawling, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub is a cabin in Pawling, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,826.

From$547/night

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Pet-friendly vacation rentals in Pawling, NY

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

10 ★ 8 reviews

Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball

Cabin, Pawling

Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball is a cabin in Pawling, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers…

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About Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball

Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball is a cabin in Pawling, with pet-friendly space, easy beach 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,728.

From$390/night

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10 ★ 3 reviews

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Cabin, Pawling

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit is a cabin in Pawling, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit is a cabin in Pawling, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,271.

From$467/night

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10 ★ 1 reviews

Peaceful Tree House Nestled Away in Hudson Valley, New York

Holiday Home, Pawling

Peaceful Tree House Nestled Away in Hudson Valley, New York is a holiday home in Pawling, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Peaceful Tree House Nestled Away in Hudson Valley, New York

Peaceful Tree House Nestled Away in Hudson Valley, New York is a holiday home in Pawling, 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: pet friendly, pets friendly, kitchen, with kitchen, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,348.

From$335/night

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9.4 ★ 8 reviews

Hidden Gem on Private Road - Hike; Swim, Ski, Sauna; Relax - Repeat!!

Holiday Home, Pawling

Hidden Gem on Private Road - Hike; Swim, Ski, Sauna; Relax - Repeat!! is a holiday home in Pawling, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a…

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About Hidden Gem on Private Road - Hike; Swim, Ski, Sauna; Relax - Repeat!!

Hidden Gem on Private Road - Hike; Swim, Ski, Sauna; Relax - Repeat!! is a holiday home in Pawling, with pet-friendly space, pool 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,864.

From$409/night

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Vacation rentals with a pool in Pawling, NY

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

10 ★ 1 reviews

9,000 Sq Ft Candlewood Lakefront Luxury - Pool, Dock, Professionally Designed

Holiday Home, Pawling

9,000 Sq Ft Candlewood Lakefront Luxury - Pool, Dock, Professionally Designed is a holiday home in Pawling, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About 9,000 Sq Ft Candlewood Lakefront Luxury - Pool, Dock, Professionally Designed

9,000 Sq Ft Candlewood Lakefront Luxury - Pool, Dock, Professionally Designed is a holiday home in Pawling, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $14,118.

From$2,017/night

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9.4 ★ 8 reviews

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Villa, Pawling

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT is a villa in Pawling, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT is a villa in Pawling, 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: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,783.

From$1,112/night

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ESKape Manor: Great Views, Hot Tub & Fun Amenities

Cabin, Pawling

ESKape Manor: Great Views, Hot Tub & Fun Amenities is a cabin in Pawling, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About ESKape Manor: Great Views, Hot Tub & Fun Amenities

ESKape Manor: Great Views, Hot Tub & Fun Amenities is a cabin in Pawling, 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, hot tub, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,876.

From$554/night

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

Villa, Pawling

Charming 2-bedroom villa in serene Holmes with AC, WiFi is a villa in Pawling, 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 Pawling, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,782.

From$683/night

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Vacation rentals with parking in Pawling, NY

Find vacation rentals that make arriving by car easier.

10 ★ 17 reviews

Beautiful Lake View House Overlooking Peaceful Whaley Lake

Holiday Home, Pawling

Beautiful Lake View House Overlooking Peaceful Whaley Lake is a holiday home in Pawling, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beautiful Lake View House Overlooking Peaceful Whaley Lake

Beautiful Lake View House Overlooking Peaceful Whaley Lake is a holiday home in Pawling, 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, kitchen, with kitchen, gym, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,339.

From$620/night

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10 ★ 3 reviews

Collins Estate East Wing Efficiency 2 bed 2 bath, AC, in Lagrangeville, NY

Apartment, Pawling

Collins Estate East Wing Efficiency 2 bed 2 bath, AC, in Lagrangeville, NY is a apartment in Pawling, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Collins Estate East Wing Efficiency 2 bed 2 bath, AC, in Lagrangeville, NY

Collins Estate East Wing Efficiency 2 bed 2 bath, AC, in Lagrangeville, NY is a apartment in Pawling, 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 cancellation, parking, free parking, ac, and air conditioning.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,426.

From$347/night

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9.8 ★ 6 reviews

Welcome to Hat City Danbury | A Suburban Retreat Close to It All

Apartment, Pawling

Welcome to Hat City Danbury · A Suburban Retreat Close to It All is a apartment in Pawling, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Welcome to Hat City Danbury | A Suburban Retreat Close to It All

Welcome to Hat City Danbury · A Suburban Retreat Close to It All is a apartment in Pawling, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,582.

From$226/night

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9.4 ★ 6 reviews

3 BR Lake House in Gated Candlewood Lake Community

Holiday Home, Pawling

3 BR Lake House in Gated Candlewood Lake Community is a holiday home in Pawling, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 3 BR Lake House in Gated Candlewood Lake Community

3 BR Lake House in Gated Candlewood Lake Community is a holiday home in Pawling, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,532.

From$362/night

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Vacation rentals with a kitchen in Pawling, NY

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

9.8 ★ 115 reviews

Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct

Holiday Home, Pawling

Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct is a holiday home in Pawling, with easy beach access and kitchen access. This stay gives travelers a…

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About Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct

Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct is a holiday home in Pawling, with easy beach 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,234.

From$605/night

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9.8 ★ 36 reviews

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Holiday Home, Pawling

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger is a holiday home in Pawling, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger is a holiday home in Pawling, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,264.

From$609/night

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8 ★ 1 reviews

Ann Inn - Downtown Milford Apartment

Apartment, Pawling

Ann Inn - Downtown Milford Apartment is a apartment in Pawling, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Ann Inn - Downtown Milford Apartment

Ann Inn - Downtown Milford Apartment is a apartment in Pawling, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,171.

From$310/night

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Trailside Base w/ Gazebo & Kayaks

Apartment, Pawling

Trailside Base w/ Gazebo & Kayaks is a apartment in Pawling, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Trailside Base w/ Gazebo & Kayaks

Trailside Base w/ Gazebo & Kayaks is a apartment in Pawling, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,736.

From$193/night

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