Vacation rentals in Dutchess County, NY

Best vacation rentals and Airbnb offers in Dutchess County, NY

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

Apartment, Dutchess County

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

Read more

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 Dutchess County, 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

Show›

Tranquil 1-bedroom apartment with AC in charming Poughkeepsie

Apartment, Dutchess County

Tranquil 1-bedroom apartment with AC in charming Poughkeepsie is a apartment in Dutchess County, with room for a group. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Tranquil 1-bedroom apartment with AC in charming Poughkeepsie

Tranquil 1-bedroom apartment with AC in charming Poughkeepsie is a apartment in Dutchess County, with 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, washer, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,623.

From$232/night

Show›

Romantic Log Cabin on Privately-Owned Lake with Fireplace

Cabin, Dutchess County

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

Read more

About Romantic Log Cabin on Privately-Owned Lake with Fireplace

Romantic Log Cabin on Privately-Owned Lake with Fireplace is a cabin in Dutchess County, 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

Show›

The Farm at Hyde Park

Holiday Home, Dutchess County

The Farm at Hyde Park is a holiday home in Dutchess County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About The Farm at Hyde Park

The Farm at Hyde Park is a holiday home in Dutchess County, 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 $2,024.

From$289/night

Show›

Vacation rentals with a pool in Dutchess County, NY

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

Romantic Sunset -50 Mile Sunset Hudson River View!

Apartment, Dutchess County

Romantic Sunset -50 Mile Sunset Hudson River View! is a apartment in Dutchess County, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Romantic Sunset -50 Mile Sunset Hudson River View!

Romantic Sunset -50 Mile Sunset Hudson River View! is a apartment in Dutchess County, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,142.

From$306/night

Show›

Private and Tranquil Country Retreat

Holiday Home, Dutchess County

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

Read more

About Private and Tranquil Country Retreat

Private and Tranquil Country Retreat is a holiday home in Dutchess County, 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

Show›

Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay

Holiday Home, Dutchess County

Historic Barn Retreat w/ Pool & Pond Views · Longview Pond Lodge by AvantStay is a holiday home in Dutchess County, with pool access, kitchen access, and a quieter setting. This stay gives…

Read more

About Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay

Historic Barn Retreat w/ Pool & Pond Views · Longview Pond Lodge by AvantStay is a holiday home in Dutchess County, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,604.

From$801/night

Show›

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook

Holiday Home, Dutchess County

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook is a holiday home in Dutchess County, with pool access and kitchen access. This stay gives travelers a comfortable…

Read more

About Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook is a holiday home in Dutchess County, 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: pool, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,705.

From$815/night

Show›

Vacation rentals with parking in Dutchess County, NY

Find vacation rentals that make arriving by car easier.

Beautiful mountaintop getaway for peace and quiet

Holiday Home, Dutchess County

Beautiful mountaintop getaway for peace and quiet is a holiday home in Dutchess County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Beautiful mountaintop getaway for peace and quiet

Beautiful mountaintop getaway for peace and quiet is a holiday home in Dutchess County, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,372.

From$339/night

Show›

The Gables of Rhinebeck Inn

Guest House, Dutchess County

The Gables of Rhinebeck Inn is a guest house in Dutchess County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About The Gables of Rhinebeck Inn

The Gables of Rhinebeck Inn is a guest house in Dutchess County, 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, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,101.

From$363/night

Show›

Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility

Guest House, Dutchess County

Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility is a guest house in Dutchess County, with parking, kitchen access, and a quieter setting. This stay gives…

Read more

About Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility

Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility is a guest house in Dutchess County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,585.

From$369/night

Show›

Hudson Valley stunning lake side modern barn in an Enchanted Forest

Holiday Home, Dutchess County

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

Read more

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 Dutchess County, 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

Show›

Pet-friendly vacation rentals in Dutchess County, NY

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

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

Holiday Home, Dutchess County

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

Read more

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

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Dutchess County, 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

Show›

The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia

Holiday Home, Dutchess County

The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia is a holiday home in Dutchess County, with pet-friendly space, pool access, and kitchen access. This stay…

Read more

About The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia

The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia is a holiday home in Dutchess County, 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 $2,730.

From$390/night

Show›

Secluded Getaway with Catskill Mountain Views

Holiday Home, Dutchess County

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

Read more

About Secluded Getaway with Catskill Mountain Views

Secluded Getaway with Catskill Mountain Views is a holiday home in Dutchess County, 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 $3,293.

From$470/night

Show›

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

Holiday Home, Dutchess County

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

Read more

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 Dutchess County, 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

Show›

Vacation rentals with a kitchen in Dutchess County, NY

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

Skyloft Mountaintop<br>Glorious privacy amidst the treetops!!

Guest House, Dutchess County

Skyloft Mountaintop<br>Glorious privacy amidst the treetops!! is a guest house in Dutchess County, with pool access, kitchen access, and room for a group. This stay gives travelers a…

Read more

About Skyloft Mountaintop<br>Glorious privacy amidst the treetops!!

Skyloft Mountaintop<br>Glorious privacy amidst the treetops!! is a guest house in Dutchess County, with pool access, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,403.

From$343/night

Show›

Charming former church near the Hudson w/ hot tub. A tranquil retreat.

Holiday Home, Dutchess County

Charming former church near the Hudson w/ hot tub. A tranquil retreat. is a holiday home in Dutchess County, with kitchen access and a quieter setting. This stay gives travelers a…

Read more

About Charming former church near the Hudson w/ hot tub. A tranquil retreat.

Charming former church near the Hudson w/ hot tub. A tranquil retreat. is a holiday home in Dutchess County, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,509.

From$358/night

Show›

Staatsburg Parsonage - A tranquil 4-bedroom house with AC

Holiday Home, Dutchess County

Staatsburg Parsonage - A tranquil 4-bedroom house with AC is a holiday home in Dutchess County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About Staatsburg Parsonage - A tranquil 4-bedroom house with AC

Staatsburg Parsonage - A tranquil 4-bedroom house with AC is a holiday home in Dutchess County, 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,782.

From$397/night

Show›

Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC

Holiday Home, Dutchess County

Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC is a holiday home in Dutchess County, with pet-friendly space and kitchen access. This stay gives travelers a…

Read more

About Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC

Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC is a holiday home in Dutchess County, 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 $6,027.

From$861/night

Show›

Family-friendly vacation rentals in Dutchess County, NY

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

Charming Rhinebeck Cottage, 5 min. from town, King Bed!

Cottage, Dutchess County

Charming Rhinebeck Cottage, 5 min. from town, King Bed! is a cottage in Dutchess County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Charming Rhinebeck Cottage, 5 min. from town, King Bed!

Charming Rhinebeck Cottage, 5 min. from town, King Bed! is a cottage in Dutchess County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,238.

From$320/night

Show›

The Secret Cottage-Hidden Gem! Entire cottage with covered patio!

Cottage, Dutchess County

The Secret Cottage-Hidden Gem! Entire cottage with covered patio! is a cottage in Dutchess County, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable…

Read more

About The Secret Cottage-Hidden Gem! Entire cottage with covered patio!

The Secret Cottage-Hidden Gem! Entire cottage with covered patio! is a cottage in Dutchess County, with outdoor 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,306.

From$329/night

Show›

West Park/Esopus Victorian - 2 King and 1 Queen Bed

Cottage, Dutchess County

West Park/Esopus Victorian - 2 King and 1 Queen Bed is a cottage in Dutchess County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About West Park/Esopus Victorian - 2 King and 1 Queen Bed

West Park/Esopus Victorian - 2 King and 1 Queen Bed is a cottage in Dutchess County, 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 $2,424.

From$346/night

Show›

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

Holiday Home, Dutchess County

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat is a holiday home in Dutchess County, with kitchen access, room for a group, and a quieter setting. This stay gives travelers a…

Read more

About Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat is a holiday home in Dutchess County, with kitchen access, room for a group, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,883.

From$412/night

Show›