Vacation rentals in Water Mill

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Top-rated vacation rentals in Water Mill

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

Guest favourite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.
Nov. 14 – 21
$342 CAD per night
4.88 out of 5 average rating, 308 reviews
Guest favourite
Guesthouse in Southampton
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!
Aug. 28 – Sep. 4
$568 CAD per night
4.95 out of 5 average rating, 411 reviews
Guest favourite
Cottage in Southampton
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.
Apr. 11 – 18
$586 CAD per night
4.96 out of 5 average rating, 162 reviews

Popular amenities for Water Mill vacation rentals

Stay near Water Mill's top sights

Parrish Art Museum263 locals recommend
Flying Point Beach46 locals recommend
Stony Brook Southampton Hospital13 locals recommend
Hampton Classic Horse Show Inc10 locals recommend
Hampton Coffee Company28 locals recommend
Hampton Jitney54 locals recommend

Other great vacation rentals in Water Mill

Guest favourite
Home in Southampton
Bay View Stunner, Modern 6 Bedroom w Heated Pool
Apr. 10 – 17
$541 CAD per night
5.0 out of 5 average rating, 36 reviews
Guest favourite
Home in Water Mill
Astounding Watermill 5 Bedroom home with Pool
May 28 – Jun. 4
$1,407 CAD per night
4.91 out of 5 average rating, 94 reviews
Guest favourite
Home in Sag Harbor
Modern Residence in Sag Harbor
Apr. 28 – May 5
$728 CAD per night
4.94 out of 5 average rating, 18 reviews
Guest favourite
Home in Southampton
Perfect Lake Cottage weekend Hamptons special
Jan. 18 – 25
$1,098 CAD per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Southampton
Luxury Hamptons Poolside Paradise w/ Outdoor Sauna
Mar. 28 – Apr. 4
$1,150 CAD per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Cottage in Southampton
Towd Point Beach Treasure | 14 min walk to beach
Mar. 25 – Apr. 1
$474 CAD per night
5.0 out of 5 average rating, 14 reviews
Guest favourite
Cottage in Bridgehampton
Bridgehampton Cottage Close to Town, South of HWY
Mar. 28 – Apr. 4
$692 CAD per night
5.0 out of 5 average rating, 48 reviews
Guest favourite
Home in Southampton
Southampton Village Perfection: Pool & Village
Mar. 31 – Apr. 7
$690 CAD per night
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Southampton
Village Charmer, 5 bedrooms with pool
Apr. 5 – 12
$453 CAD per night
4.94 out of 5 average rating, 63 reviews
Guest favourite
Guesthouse in Southampton
Southampton Modern Barn, Private Hot Tub and Pool
Jul. 23 – 30
$1,290 CAD per night
4.98 out of 5 average rating, 45 reviews
Guest favourite
Cottage in Sag Harbor
Luxury Gem At The Heart of Sag Harbor Village
Apr. 27 – May 4
$851 CAD per night
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Southampton
Scandinavian Cottage
Oct. 12 – 19
$524 CAD per night
4.91 out of 5 average rating, 33 reviews

Quick stats about vacation rentals in Water Mill

Total rentals

250 properties

Rentals with a pool

210 properties have a pool

Pet-friendly rentals

130 properties allow pets

Family-friendly rentals

230 properties are a good fit for families

Total number of reviews

3.2K reviews

Nightly prices starting at

$14 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Water Mill