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Vacation rentals in Chappaqua

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Top-rated vacation rentals in Chappaqua

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Rental unit in Mount Kisco

4.92 out of 5 average rating, 172 reviews

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

This cozy apartment is on the lower level of a house, just a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mount Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

Home in Ossining

4.85 out of 5 average rating, 137 reviews

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Guesthouse in Mahopac

4.94 out of 5 average rating, 173 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ other dining/ takeout options + excellent boba tea shop! Drivable to farm fresh food markets, restaurants and art museums. Endless nearby cute towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to the trails of Volz park!

Rental unit in Peekskill

4.81 out of 5 average rating, 153 reviews

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Rental unit in Ossining

4.95 out of 5 average rating, 388 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Guesthouse in Bedford Hills

4.88 out of 5 average rating, 128 reviews

Barrett's Sanctuary

Airy, bright guest house with with access to a gunite pool, patio and expansive backyard for practicing your short game, playing disc golf or other sports. Loft (accessible by spiral staircase) furnished with queen bed. Single bed in alcove off living room. Central air/heat. Washer/dryer. Kitchenette w/ dishwasher. Satellite TV. LR w/ stone fireplace. Minutes to train (1h to Manhattan) and highways. Shopping/restaurants nearby. Delivery available from Seamless, Instacart and more.

Guest suite in Haverstraw

4.94 out of 5 average rating, 336 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Home in Pound Ridge

5 out of 5 average rating, 148 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Guesthouse in Peekskill

4.93 out of 5 average rating, 251 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Home in Mount Kisco

4.94 out of 5 average rating, 145 reviews

Incredible barn in country setting

Country setting with Vermont feel. Indoor /outdoor fireplaces with large entertainment areas. Small kitchenette, 2 BR. Pull out coach, and sleeping loft . Wifi, CAC, washer/dryer, local hiking w 3 nature preserves nearby. Major estate area. 6 min. from Mt. Kisco train station. One hour NYC. Great local restaurants. Out of the ordinary!

Barn in Mount Kisco

4.91 out of 5 average rating, 564 reviews

NY Rustic Cottage Getaway

Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

Guesthouse in Bedford

4.92 out of 5 average rating, 193 reviews

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

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Popular amenities for Chappaqua vacation rentals

Free parking on premises

Air conditioning

Stay near Chappaqua's top sights

Jacob Burns Film Center33 locals recommend

Village Social Kitchen & Bar17 locals recommend

Jacob Burns Media Arts Lab11 locals recommend

Starbucks10 locals recommend

Jean-Jacques' Culinary Creations10 locals recommend

The Black Cow Coffee Company9 locals recommend

Other great vacation rentals in Chappaqua

Home in Katonah

5 out of 5 average rating, 13 reviews

The Cottage at Fern Hill

Rental unit in Pleasantville

4.82 out of 5 average rating, 57 reviews

Beautiful Studio Apartment in Perfect Location

Guesthouse in Bedford Hills

5 out of 5 average rating, 26 reviews

The Perch, a luxe cottage in the woods 1h from NYC

Home in Ossining

4.86 out of 5 average rating, 21 reviews

Hudson Valley Escape

Rental unit in Mount Kisco

4.9 out of 5 average rating, 73 reviews

Clean,Comfy & Convenient. Private 1Bed Village Apt

Home in Bedford

5 out of 5 average rating, 29 reviews

Comfortable Mid-Century on Quiet Country Road

Home in Briarcliff Manor

4.94 out of 5 average rating, 33 reviews

Quaint Cottage in the Woods

Guesthouse in Chappaqua

4.86 out of 5 average rating, 28 reviews

Comfortable, clean studio guesthouse in Chappaqua

Quick stats about vacation rentals in Chappaqua

Total rentals
20 properties
Total number of reviews
500 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Frequently Asked Questions

What are the most popular amenities for House Rentals in Chappaqua?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Chappaqua?
Chappaqua has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Chappaqua?
Yes! Work meets play with ease at over 10 vacation rentals in Chappaqua featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Chappaqua have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Chappaqua. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chappaqua?
Experience the best of Chappaqua with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chappaqua have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Chappaqua. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chappaqua have wifi?
Absolutely! We offer over 10 house rentals with wifi in Chappaqua. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chappaqua have free parking?
Absolutely! We offer over 10 house rentals with free parking in Chappaqua. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore