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Greenwich vacation rentals

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Top-rated vacation rentals in Greenwich

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

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Cottage in Cortlandt

4.99 out of 5 average rating, 167 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Cabin in Vernon Valley

4.97 out of 5 average rating, 365 reviews

Serenity Cabin, the historic waterfall cabin!

Escape to a magical paradise where the sound of a babbling stream & chirping birds create a symphony of serenity. Nestled on 18 acres of pristine wilderness, this secluded retreat offers endless opportunities for exploration & adventure. Wander along the streams and discover hidden waterfalls, all while immersing yourself in the breathtaking beauty of nature. Located 5 minutes from Mountain Creek, Warwick drive-in, Appalachian trail, & activities like goat yoga, horse riding, & TreEscape adv.

Home in Bayport

4.84 out of 5 average rating, 156 reviews

Exquisite spacious waterfront all modern-sleeps 8

READ THE CONSISTENT FINE REVIEWS! Its heart-warming providing such a nice sanctuary! This MEMORABLE Sayville / Bayport Vacation rental home has a picturesque backyard & amazing water views. 3Br 2 full bath. Enjoy the 2-person steam shower & huge 10-person whirlpool bath for spa-like living. Perfect for quiet getaways. All new furniture w/ coastal chic decor. Feed 6 ducks, 2 swans, 2 cranes. The serenity & one-of-a kind view sets this Sayville vacation home apart from all others.

Vacation home in Warren

4.99 out of 5 average rating, 125 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Home in Andover

4.95 out of 5 average rating, 274 reviews

Stay at beautiful Leisure Lake Lodge

Leisure Lake Lodge is located on beautiful Lake Hopatcong just 1 hour from NYC. You'll fall in love w/ stunning lake views from all 3 levels of this large home, two massive decks over the lake & totally updated home easily sleeps 9. Fireplace, hot tub, sauna, foosball, ping pong, grill, 65" UHD TV, fully equipped newer kitchen, newer bathrooms, newer mattresses, 50 ft lake frontage w/ 80 ft dock, 32x20 ft boathouse w/ 400 SF deck over the lake & 19x12 ft 4-season game room with ping pong.

Chalet in Goshen

4.89 out of 5 average rating, 122 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

Condo in Vernon Township

4.92 out of 5 average rating, 103 reviews

Perfect Retreat! Water park, hot tub, bike races.

Gorgeous second floor unit at the Appalachian Lodge at Mountain Creek. Steps from ski lifts, waterpark and year round outdoor pool / hot tubs. Ski locker, indoor garage. Skiing/snow tubing to mountain biking/horseback riding/farms/hiking/golf/water park & more! The Appalachian is your perfect base to explore Vernon, Sussex and nearby Warwick, NY. Renovated 1 bdr condo w/king bed, sleeper sofa, balcony, gas fireplace - the perfect getaway for a couple or small family. 1 hr to EWR or LGA.

Condo in Vernon Township

4.95 out of 5 average rating, 113 reviews

Resort Getaway-Mtn Creek-Waterpark/ Pool/Hot Tub

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Be steps away from waterpark & chairlift for mountain biking. Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Home in Baldwin

4.85 out of 5 average rating, 115 reviews

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

Cottage in Vernon Township

4.93 out of 5 average rating, 173 reviews

Rustic Chic Lake view cottage 50 miles from NYC

Cozy lake view cottage 50 miles from NYC. Nestled in nature with swimming, fishing , hiking and biking with beautiful lake views. 5 beaches to choose from. Lovely walking or jogging around the lake, Appalachian trail nearby. Highland Lakes is a very scenic, peaceful area easily accessible. 3 of the best golf courses in the US , Mountain Creek water park and resort minutes away.Apple and pumpkin picking comes fall. Beautiful village of Warwick NY is nearby with restaurants and shopping .

Chalet in Monticello

4.98 out of 5 average rating, 106 reviews

Riverfront Ski Chalet

Escape to the country air at Sean & Brad's riverfront chalet on the Neversink River. Formerly a popular ski shop and yoga studio, this fully renovated property offers you every possible amenity. Walk across the street to launch your kayak or toss a line into some of the best trout fishing around, roast s'mores around the fire or visit the Resorts World Casino, just 5 minutes away. Golf, hiking, mountain biking, local breweries and distilleries...all just a short distance as well.

Home in Port Jervis

4.94 out of 5 average rating, 222 reviews

Victorian At Orange Square Entire Home

Immediately Feel Welcome As You Walk Up On The Pillared Front Porch With Its Rocker And Lounge Chairs. Enter The Welcoming Foyer And Feel The Comfort Of Home. Sink Deep In The Stuffed Couches In Front Of The Remote Controlled Gas Fireplace.. Enjoy Your Current Favorite Book Or The Smart TV Entertainment Center. If Inclined Cook A Meal In The Modern Kitchen And Dine In The Elegant Dining Room With A Wood Burning Fireplace. FOLLOW US ON INSTAGRAM https://instagram.com/vic.torian11

Vacation rentals for every style

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Popular amenities for Greenwich vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Greenwich's top sights

Chipotle Mexican Grill111 locals recommend

The Cheesecake Factory60 locals recommend

Whole Foods Market54 locals recommend

Barcelona Wine Bar51 locals recommend

Stamford Town Center34 locals recommend

Playland Park29 locals recommend

Other great vacation rentals in Greenwich

Home in Beacon

4.89 out of 5 average rating, 109 reviews

BeaconsGreatGetaway(Firepit,backyard,bbq,crib,farm

Home in Mastic

4.94 out of 5 average rating, 117 reviews

Paradise Citadelhottub, heated pool golf

Cabin in Rocky Point

4.9 out of 5 average rating, 420 reviews

Great little place just for a couple

Home in Kerhonkson

4.9 out of 5 average rating, 242 reviews

Perfect Country Cabin getaway. Large Fenced yard.

Rental unit in Wallkill

4.95 out of 5 average rating, 129 reviews

Log Cabin Apartment Great for Outdoor Enthusiasts

Home in High Falls

4.98 out of 5 average rating, 113 reviews

Beautiful country house w/ cedar hot tub

Home in East Patchogue

4.78 out of 5 average rating, 143 reviews

Bay's Edge Vacation Get a Way

Guesthouse in Southbury

4.93 out of 5 average rating, 284 reviews

Charming Guest Cottage with Modern Amenities

Quick stats about vacation rentals in Greenwich

Total rentals
270 properties
Total number of reviews
9.4K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
170 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Greenwich?
Make yourself at home in Greenwich by choosing from our most frequently booked neighborhoods. We have over 340 vacation rentals in North Stamford, over 60 vacation rentals in Purchase, and over 50 vacation rentals in Tamarack Gardens.
Are there vacation rentals with a dedicated workspace in Greenwich?
Yes! Work meets play with ease at over 170 vacation rentals in Greenwich featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Greenwich?
Four-legged friends are welcome in Greenwich. Choose from more than 100 vacation rentals for guests traveling with pets.
Are there Greenwich vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Greenwich, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Greenwich have air conditioning?
Absolutely! We offer over 50 apartment rentals with air conditioning in Greenwich. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in bed and breakfast rentals in Greenwich?
Experience the best of Greenwich with our bed and breakfast rentals, starting at about $250 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 Greenwich have a gym?
Absolutely! We offer over 50 house rentals with a gym in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Greenwich have wifi?
Absolutely! We offer over 10 bed and breakfast rentals with wifi in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenwich have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Greenwich?
Greenwich has more than 20 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore