Vacation rentals in Dover Plains, NY

Best Vacation rentals and Airbnb offers in Dover Plains, NY

Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool

Apartment, Dover Plains

Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool is a apartment in Dover Plains, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool

Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool is a apartment in Dover Plains, with 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,369.

From$196/night

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Dainty New Preston Cottage w/ Dock & Lake Views!

Holiday Home, Dover Plains

Dainty New Preston Cottage w/ Dock & Lake Views! is a holiday home in Dover Plains, 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 Dover Plains, 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, Dover Plains

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

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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 Dover Plains, 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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Romantic Log Cabin on Privately-Owned Lake with Fireplace

Cabin, Dover Plains

Romantic Log Cabin on Privately-Owned Lake with Fireplace is a cabin in Dover Plains, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Romantic Log Cabin on Privately-Owned Lake with Fireplace

Romantic Log Cabin on Privately-Owned Lake with Fireplace is a cabin in Dover Plains, 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 $1,865.

From$266/night

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Browse Vacation Rentals with a Pool in Dover Plains, NY

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

Private and Tranquil Country Retreat

Holiday Home, Dover Plains

Private and Tranquil Country Retreat is a holiday home in Dover Plains, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Private and Tranquil Country Retreat

Private and Tranquil Country Retreat is a holiday home in Dover Plains, 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, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,954.

From$565/night

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Enjoy pool time at our spacious home; minutes from the village of Millbrook!

Holiday Home, Dover Plains

Enjoy pool time at our spacious home; minutes from the village of Millbrook! is a holiday home in Dover Plains, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Enjoy pool time at our spacious home; minutes from the village of Millbrook!

Enjoy pool time at our spacious home; minutes from the village of Millbrook! is a holiday home in Dover Plains, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,749.

From$678/night

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Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve

Holiday Home, Dover Plains

Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve is a holiday home in Dover Plains, with pool access. This stay gives travelers a comfortable base for exploring…

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About Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve

Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve is a holiday home in Dover Plains, with 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.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,375.

From$1,196/night

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House Nestled Bet Vineyards/Pool, Sauna and Spa

Holiday Home, Dover Plains

House Nestled Bet Vineyards/Pool, Sauna and Spa is a holiday home in Dover Plains, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About House Nestled Bet Vineyards/Pool, Sauna and Spa

House Nestled Bet Vineyards/Pool, Sauna and Spa is a holiday home in Dover Plains, with 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,847.

From$1,835/night

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Best Dover Plains, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Hudson Valley stunning lake side modern barn in an Enchanted Forest

Holiday Home, Dover Plains

Hudson Valley stunning lake side modern barn in an Enchanted Forest is a holiday home in Dover Plains, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Hudson Valley stunning lake side modern barn in an Enchanted Forest

Hudson Valley stunning lake side modern barn in an Enchanted Forest is a holiday home in Dover Plains, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,433.

From$490/night

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5-DAY NEW ENGLAND \"MINI-VACATION\" in SHARON CONNECTICUT

Apartment, Dover Plains

5-DAY NEW ENGLAND \"MINI-VACATION\" in SHARON CONNECTICUT is a apartment in Dover Plains, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 5-DAY NEW ENGLAND \"MINI-VACATION\" in SHARON CONNECTICUT

5-DAY NEW ENGLAND \"MINI-VACATION\" in SHARON CONNECTICUT is a apartment in Dover Plains, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,645.

From$521/night

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

Holiday Home, Dover Plains

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

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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 Dover Plains, 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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Beautiful Lake View House Overlooking Peaceful Whaley Lake

Holiday Home, Dover Plains

Beautiful Lake View House Overlooking Peaceful Whaley Lake is a holiday home in Dover Plains, 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 Dover Plains, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,451.

From$636/night

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Best Pet-Friendly Vacation Rentals in Dover Plains, NY

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

Fire Pit + On-Site Pond: Hudson Valley Home!

Holiday Home, Dover Plains

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Dover Plains, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Fire Pit + On-Site Pond: Hudson Valley Home!

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Dover Plains, 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 $2,750.

From$295/night

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Fire Pit + On-Site Pond: Hudson Valley Home!

Holiday Home, Dover Plains

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Dover Plains, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Fire Pit + On-Site Pond: Hudson Valley Home!

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Dover Plains, 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 $2,576.

From$368/night

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Secluded Getaway with Catskill Mountain Views

Holiday Home, Dover Plains

Secluded Getaway with Catskill Mountain Views is a holiday home in Dover Plains, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Secluded Getaway with Catskill Mountain Views

Secluded Getaway with Catskill Mountain Views is a holiday home in Dover Plains, 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, hot tub, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,229.

From$461/night

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YOIN: Whispers of Tranquility, a Zen Retreat

Holiday Home, Dover Plains

YOIN: Whispers of Tranquility, a Zen Retreat is a holiday home in Dover Plains, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About YOIN: Whispers of Tranquility, a Zen Retreat

YOIN: Whispers of Tranquility, a Zen Retreat is a holiday home in Dover Plains, with pet-friendly space 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, pet friendly, pets friendly, gym, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,601.

From$514/night

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Best Dover Plains, NY vacation rentals with a kitchen

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

Incredible spacious family friendly getaway

Holiday Home, Dover Plains

Incredible spacious family friendly getaway is a holiday home in Dover Plains, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Incredible spacious family friendly getaway

Incredible spacious family friendly getaway is a holiday home in Dover Plains, with 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,763.

From$538/night

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One of the Original Summer Cottages on Lake Warmaug

Holiday Home, Dover Plains

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

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

Holiday Home, Dover Plains

Beautiful lake view home on Whaley Lake in Holmes, NY. is a holiday home in Dover Plains, 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 Dover Plains, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,491.

From$642/night

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Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit

Holiday Home, Dover Plains

Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit is a holiday home in Dover Plains, with kitchen access and room for a group. This stay gives travelers a…

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About Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit

Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit is a holiday home in Dover Plains, with 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,277.

From$754/night

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Our Favorite Family-Friendly Vacation Rentals in Dover Plains, NY

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

Dainty New Preston Cottage w/ Dock & Lake Views!

Cottage, Dover Plains

Dainty New Preston Cottage w/ Dock & Lake Views! is a cottage in Dover Plains, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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

Dainty New Preston Cottage w/ Dock & Lake Views! is a cottage in Dover Plains, 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 $2,179.

From$311/night

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Fire Pit + On-site Pond: Hudson Valley Home!

Cottage, Dover Plains

Fire Pit + On-site Pond: Hudson Valley Home! is a cottage in Dover Plains, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Fire Pit + On-site Pond: Hudson Valley Home!

Fire Pit + On-site Pond: Hudson Valley Home! is a cottage in Dover Plains, 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 $2,852.

From$334/night

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Litchfield Hills 3BR New Milford Retreat with Ravine Views & Covered Porch

Cottage, Dover Plains

Litchfield Hills 3BR New Milford Retreat with Ravine Views & Covered Porch is a cottage in Dover Plains, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Litchfield Hills 3BR New Milford Retreat with Ravine Views & Covered Porch

Litchfield Hills 3BR New Milford Retreat with Ravine Views & Covered Porch is a cottage in Dover Plains, 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 $3,329.

From$476/night

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Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Holiday Home, Dover Plains

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway is a holiday home in Dover Plains, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers…

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About Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway is a holiday home in Dover Plains, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,361.

From$480/night

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