Vacation rentals in Water Mill

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Top-rated vacation rentals in Water Mill

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Guest favorite

Guesthouse in Southampton

4.95 out of 5 average rating, 411 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

Oct 6 – 13

G$68,149 GYD per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 163 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Oct 23 – 30

G$101,482 GYD per night

Guest favorite

Loft in Water Mill

5.0 out of 5 average rating, 12 reviews

Cozy ,Renovated Apartment for single or couple

Nice ,newly renovated basement apartment with natural light. high ceilings, walk out patio door, private entrance, soundproofed, washer/dryer, dishwasher , radiant heated bathroom floor, independent heating and cooling system from main house, off street parking for one vehicle, perfect for single or couple. Centrally located for all fall activities, farm stands, apple picking, Film Fest, Dining , shopping. This apartment has been vacant since last summer and since being renovated.

May 24 – 31

G$59,834 GYD per night

Guest favorite

Cottage in Southampton

4.97 out of 5 average rating, 99 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Aug 16 – 23

G$202,845 GYD per night

Superhost

Home in Water Mill

4.81 out of 5 average rating, 16 reviews

Charming Water Mill Get Away

Beautiful home on a quiet street. Immaculately maintained. In addition to five bedrooms and three bathrooms, this home boasts two living rooms and sunlight throughout to create a wonderfully bright feel. Country style kitchen for indoor cooking and a grill for outdoor BBQ's. Beautiful outdoor space with mature trees, lawn, a huge charming barn, teak garden furniture and a large swimming pool. Indoor movie theater and ping pong table. Your perfect Hampton's stay starts right here!

Nov 30 – Dec 7

G$112,625 GYD per night

Guest favorite

Home in Southampton

4.91 out of 5 average rating, 179 reviews

Peaceful Hamptons Cottage

Looking for a getaway? Nestled into one of the largest preserves in the Hamptons, this sunny newly renovated beachy cottage is the perfect retreat. The legendary Hamptons beaches, wineries, Southampton Village, and the world famous golf courses are less than a 10 minute drive away. There are many nearby essential shops, farm stands & restaurants. Set up for WFH with hi-speed wifi and a desk. Abuts a large nature preserve with hiking paths. Lots of deer will roam by your window!

Aug 20 – 27

G$133,026 GYD per night

Guest favorite

Home in Southampton

4.9 out of 5 average rating, 213 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Jun 5 – 12

G$120,300 GYD per night

Guest favorite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Your modern, spacious, sparkling clean guest home has 2 private floors and a private entrance. The bedroom provides luxury and calm as light from the green trees filters in. Watch movies & chill in your living room complete with kitchenette, wine cooler, powder room and adjoining dining space. You’re in a peaceful neighborhood facing a land forest preserve, 5 minutes from bay beaches and the plethora of farm fresh, organic Sag Harbor eateries.

Feb 1 – 8

G$88,362 GYD per night

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

Oct 10 – 17

G$156,074 GYD per night

Guest favorite

Home in Water Mill

4.92 out of 5 average rating, 91 reviews

Peaceful 1850s barn w/Pool

Family, friends and work-friendly property. Sleeps 8 (+2) in 4 bedrooms with 3 bathrooms. Tranquil 3000 sq ft house w/heated pool (pool season circa May 21 to Sept 20) set in 1.7 quiet acres off private driveway. Large garden and fenced pool area. Fresh in summer, cozy w/log fires in winter. Minutes from beautiful beaches, Water Mill's historic charm and the visual & performing arts. A simple but stylish and very comfortable house!

Oct 29 – Nov 5

G$164,697 GYD per night

Guest favorite

Home in Water Mill

4.88 out of 5 average rating, 72 reviews

Charming Water Mill Cottage

This cottage is part of a compound consisting of a main house and pool house/studio. It has a King Size Bed in the bedroom; a Cozy Eat in Kitchen with a full size Stove and Microwave, along with a Full Size Fridge. There's plenty of seating in the Living-Room, that also has a pull out couch, as well as a Fully Tiled Bathroom. There's a large private patio with hedged in fence. It's the perfect space for relaxing.

Dec 26 – Jan 2

G$49,803 GYD per night

Guest favorite

Cottage in Water Mill

4.98 out of 5 average rating, 55 reviews

Head of Pond House - Waterfront Cottage

Charming Cottage with lake access. Close to beaches, wineries, restaurants and all the Hamptons have to offer. One bedroom, and two king beds (one in the loft area), one bath cottage with WIFI and projector. Kitchen including fridge, stove, oven and dishwasher for your perfect weekend or weeklong getaway. Ideal for anyone looking for a peaceful oasis while close to all the action of the East End.

Apr 28 – May 5

G$107,675 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Water Mill vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Water Mill's top sights

Parrish Art Museum263 locals recommend

Hampton Classic Horse Show Inc10 locals recommend

Flying Point Beach46 locals recommend

Stony Brook Southampton Hospital13 locals recommend

Hampton Coffee Company28 locals recommend

Hampton Jitney54 locals recommend

Other great vacation rentals in Water Mill

Guest favorite

Home in Water Mill

5.0 out of 5 average rating, 79 reviews

Pristine 5 bedroom Home - South of the Highway

May 16 – 23

G$214,837 GYD per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 55 reviews

Dream home in SH with heated private Pool

Jan 13 – 20

G$103,767 GYD per night

Guest favorite

Home in Sag Harbor

4.84 out of 5 average rating, 45 reviews

Modern Home in Sag Harbor, NY

Sep 11 – 18

G$156,325 GYD per night

Guest favorite

Home in Water Mill

4.82 out of 5 average rating, 66 reviews

Lovely Hamptons Home

Oct 20 – 27

G$129,840 GYD per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 21 reviews

Renovated Southampton Home+Pool

Nov 22 – 29

G$75,884 GYD per night

Superhost

Home in Water Mill

4.86 out of 5 average rating, 14 reviews

Water Mill Oasis w/ Pool Close to Beach&Village!

Sep 26 – Oct 3

G$231,872 GYD per night

Guest favorite

Guesthouse in Southampton

4.98 out of 5 average rating, 45 reviews

Southampton Modern Barn, Private Hot Tub and Pool

Sep 11 – 18

G$137,134 GYD per night

Guest favorite

Home in Sag Harbor

4.96 out of 5 average rating, 26 reviews

Sag Harbor Chic Mid-Century retreat.

Sep 14 – 21

G$137,019 GYD per night

Show all

Quick stats about vacation rentals in Water Mill

Total rentals
240 properties
Rentals with a pool
200 properties have a pool
Pet-friendly rentals
130 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
3.1K reviews
Nightly prices starting at
G$2,090 GYD before taxes and fees

Frequently Asked Questions

Do cottage rentals in Water Mill have free parking?
Absolutely! We offer over 10 cottage rentals with free parking in Water Mill. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Water Mill have a kitchen?
Absolutely! We offer over 10 cottage rentals with a kitchen in Water Mill. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cottage rentals in Water Mill?
Experience the best of Water Mill with our cottage rentals, starting at about $370 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Water Mill?
Water Mill has more than 220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there Water Mill vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 200 vacation homes with pools in Water Mill, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Water Mill?
Four-legged friends are welcome in Water Mill. Choose from more than 130 vacation rentals for guests traveling with pets.
Do house rentals in Water Mill have air conditioning?
Absolutely! We offer over 190 house rentals with air conditioning in Water Mill. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Water Mill have wifi?
Absolutely! We offer over 200 house rentals with wifi in Water Mill. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Water Mill?
Yes! Work meets play with ease at over 140 vacation rentals in Water Mill featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Water Mill?
Enhance your stay in our House Rentals with the most popular amenities: over 200 homes with wifi, over 200 homes with a kitchen, over 190 homes with free parking, over 190 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Water Mill

Top-rated vacation rentals in Water Mill

Vacation rentals for every style

Houses

Villas

Hotels

Popular amenities for Water Mill vacation rentals

Stay near Water Mill's top sights

Other great vacation rentals in Water Mill

Home in Water Mill

Home in Southampton

Home in Sag Harbor

Home in Water Mill

Home in Southampton

Home in Water Mill

Guesthouse in Southampton

Home in Sag Harbor

Quick stats about vacation rentals in Water Mill

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do cottage rentals in Water Mill have free parking?

Do cottage rentals in Water Mill have a kitchen?

How much does it cost to stay in cottage rentals in Water Mill?

Are there family-friendly vacation rentals in Water Mill?

Are there Water Mill vacation rentals on Airbnb with pools?

Are there pet-friendly vacation rentals in Water Mill?

Do house rentals in Water Mill have air conditioning?

Do house rentals in Water Mill have wifi?

Are there vacation rentals with a dedicated workspace in Water Mill?

What are the most popular amenities for House Rentals in Water Mill?

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