Vacation rentals in Southampton

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Top-rated vacation rentals in Southampton

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

Guest favourite
Guesthouse in Hampton Bays
WELCOME TO THE LOVE SHACK BY THE SEA
Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.
May 21 – 28
$643 CAD per night
4.96 out of 5 average rating, 145 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 Southampton vacation rentals

Stay near Southampton's top sights

Citarella Gourmet Market - Southampton66 locals recommend
Tate's Bake Shop76 locals recommend
Stony Brook Southampton Hospital13 locals recommend
75 Main36 locals recommend
Saaz19 locals recommend
Southampton Publick House37 locals recommend

Other great vacation rentals in Southampton

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
Home in Southampton
Tranquility at the Water’s Edge
Feb. 15 – 22
$858 CAD per night
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Southampton
Beautiful Southampton Village Home with Pool
Nov. 10 – 17
$1,003 CAD per night
4.97 out of 5 average rating, 35 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
Scandinavian Cottage
Oct. 12 – 19
$524 CAD per night
4.91 out of 5 average rating, 33 reviews
Guest favourite
Home in Water Mill
WaterMill Oasis w/ Pool Close to Beach&Village!
Mar. 23 – 30
$800 CAD per night
4.86 out of 5 average rating, 14 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
Home in Sag Harbor
Modern Home in Sag Harbor, NY
May 16 – 23
$1,130 CAD per night
4.84 out of 5 average rating, 45 reviews
Guest favourite
Home in Southampton
Classic Southampton Village Home w/ Pool
May 29 – Jun. 5
$1,109 CAD per night
4.89 out of 5 average rating, 63 reviews
Guest favourite
Cottage in Southampton
Modern Southampton Cottage | Heated Pool & Peloton
Sep. 18 – 25
$965 CAD per night
4.93 out of 5 average rating, 60 reviews
Guest favourite
Home in Southampton
Renovated Southampton Home+Pool
Jan. 12 – 19
$550 CAD per night
5.0 out of 5 average rating, 20 reviews
Guest favourite
Apartment in Southampton
Sunny one bedroom in Southampton
Jun. 1 – 8
$630 CAD per night
5.0 out of 5 average rating, 15 reviews

Quick stats about vacation rentals in Southampton

Total rentals

640 properties

Rentals with a pool

340 properties have a pool

Pet-friendly rentals

260 properties allow pets

Family-friendly rentals

390 properties are a good fit for families

Total number of reviews

7.3K reviews

Nightly prices starting at

$14 CAD before taxes and fees

Destinations to explore

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  2. United States
  3. New York
  4. Suffolk County
  5. Southampton