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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 Greenwood Lake

4.93 out of 5 average rating, 169 reviews

Cozy home in the Village of Greenwood Lake

Adorable country retreat under an hour from NYC - perfect for a romantic couples getaway or a family of 4. Located in the village, our quaint cottage is walkable to everything; Restaurants, bars, grocer, cvs, bagels, bus stop and even the public beach!! Minutes away from TONS of local attractions; drive-in, skiing, renaissance fair, wineries, shopping, lake activities, orchards, creameries, parks, Appalachian trail, spa, rafting, golf, water park, & so much more. Pets welcome! Permit #21-07603

Home in Greenwood Lake

5 out of 5 average rating, 111 reviews

Time to escape to the lake!Hot-tub/1 hour from NYC

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

Cottage in Greenwood Lake

4.84 out of 5 average rating, 103 reviews

Lake Cottage / Sauna, Hot Tub, Beach Access

Private Quiet Lakehouse with Hot Tub and Sauna that sits beautifully on a cliff with views of the glorious natural Greenwood Lake. This cottage was built in 1935 with a large wood burning fireplace to end your day in pure comfort. Take a week or take a long weekend with the cottage just a hop skip and jump away from the city. Perfect for close friends or family to escape for some fresh air, wildlife, hiking, wineries, and the smell of fresh water. Access to community private beach.STR#:33466

Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Cabin in Vernon Valley

4.97 out of 5 average rating, 391 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.

Vacation home in Warren

4.98 out of 5 average rating, 145 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

Condo in Vernon Township

4.74 out of 5 average rating, 110 reviews

200 yards from Minerals - great location

Our place is super clean Located at the center of the mountain at Granite ski lift. 100 ft from lift. The closest condo to Minerals Resort and Spa. Ideal for wedding stay for both Minersls as well as Crystal springs resorts. Off ski season affords you the great opportunity to explore waterpark, farms, wineries, lakes and hike-Appalachian trail while enjoying mountain views and beautiful sunsets. We are footsteps away from the lift. Beautiful for all seasons! We are in Great Gorge Village

Home in Bayport

4.83 out of 5 average rating, 161 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.

Condo in Vernon Township

4.91 out of 5 average rating, 112 reviews

Perfect Retreat! Ski in/out, 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.

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Cottage in Vernon Township

4.94 out of 5 average rating, 190 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 .

Guesthouse in Warwick

5 out of 5 average rating, 208 reviews

Cottage at Millpond Falls - Romantic Luxury Escape

Looking for a romantic getaway? Relax in this restored cottage overlooking a waterfall in a private setting. We offer a 5-star premium experience! Super-clean and luxurious. Our most frequent review: "We can't wait to come back!" Nearby wineries, craft breweries. Minutes from Warwick village, restaurants, bars, antiques and shopping, Appalachian Trail, and Greenwood Lake. Winter skiing or summer water park nearby. Close to LegoLand and Jehovah's Witness Headquarters.

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

Guesthouse in Southbury

4.94 out of 5 average rating, 309 reviews

Charming Guest Cottage with Modern Amenities

Home in New Paltz

4.89 out of 5 average rating, 137 reviews

A waltz in the paltz

Cottage in Cortlandt

4.99 out of 5 average rating, 177 reviews

The Little Cottage in the Woods

Cabin in Phillipsport

4.97 out of 5 average rating, 197 reviews

The Pond House - A modern cabin within the forest.

Home in Garrison

4.93 out of 5 average rating, 157 reviews

Hudson Valley Mountaintop Riverview

Cottage in Greenwood Lake

4.85 out of 5 average rating, 182 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

Cabin in Vernon Township

4.83 out of 5 average rating, 109 reviews

All year cabin escape from NYC - near Mt. Creek!

Tiny home in Poughkeepsie

4.85 out of 5 average rating, 106 reviews

Lake Side Tiny House

Quick stats about vacation rentals in Greenwich

Total rentals
290 properties
Total number of reviews
10K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
180 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 370 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 180 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 110 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 private suite rentals in Greenwich?
Experience the best of Greenwich with our private suite rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Greenwich have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in Greenwich have wifi?
Absolutely! We offer over 10 private suite rentals with wifi in Greenwich. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Greenwich have a bbq area?
Absolutely! We offer over 10 apartment 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.

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