Search Town of Southampton Cottage Rentals from CA $411

Compare and save

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Top Cities in Town of Southampton

CottagesCottages

Riverhead

Riverhead

Featured Cottages in Town of Southampton

Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is CA $687
CA $1,333 total
includes taxes & fees
Aug 13 - Aug 14
Southampton cozy cottage by the beach
Location and views! Located directly on Shinnecock Bay!
Smart TV

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (27)
"Cute beach bungalow vibe. The outdoor space, grill, and firepit made this property worthwhile! Lori's a wonderful, accomodating host."
Location and views! Located directly on Shinnecock Bay!
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool
CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE
Property grounds

CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE

10.0 out of 10, Exceptional, (13)
"We had a wonderful stay here while visiting for a wedding. the bedrooms were both upstairs, FYI which I wasn't aware of from the listing but we made it work. The grounds were beautiful and lots of birds to enjoy. "
CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE
Town walking distance-Bridgehampton Cottage
Beach nearby

Town walking distance-Bridgehampton Cottage

9.4 out of 10, Exceptional, (10)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
Town walking distance-Bridgehampton Cottage
Hidden gem! Southampton beach cottage
Smart TV

Hidden gem! Southampton beach cottage

The price is CA $411
CA $979 total
includes taxes & fees
Aug 13 - Aug 14
Hidden gem! Southampton beach cottage
Hamptons Vacation Rental w/ Seasonal Pool!
Cottage (3 Bedrooms) | Interior

Hamptons Vacation Rental w/ Seasonal Pool!

3.0 star property
Hamptons Vacation Rental w/ Seasonal Pool!
Charming and Bright Cottage with Salt Water Pool
Smart TV

Charming and Bright Cottage with Salt Water Pool

10.0 out of 10, Exceptional, (8)
"What a beautiful cottage. Clean and bright. Would definitely stay again!"
Charming and Bright Cottage with Salt Water Pool
Hampton Cottage.
Smart TV, fireplace

Hampton Cottage.

10.0 out of 10, Exceptional, (4)
"we had a great stay at this property. the house was perfect. great value for the price. it is new and modern and extremely clean. the area itself was also nice. on a dead end street so nice and secluded. the host also included many amenities for guests to use which was a plus. would definitely stay here again. "
Hampton Cottage.
Waterfront Home w/ Large Deck + Private Pool!
Interior

Waterfront Home w/ Large Deck + Private Pool!

3.0 star property
Waterfront Home w/ Large Deck + Private Pool!
Hamptons Bay Home on Shinnecock Bay w/ Yard!
House (2 Bedrooms) | Interior

Hamptons Bay Home on Shinnecock Bay w/ Yard!

3.0 star property
Hamptons Bay Home on Shinnecock Bay w/ Yard!
Southampton Beach & Town Cottage
Pool

Southampton Beach & Town Cottage

10.0 out of 10, Exceptional, (3)
"Close to everything we wanted to do."
Southampton Beach & Town Cottage
Charming Hampton Bays Home 5 Mi to Coopers Beach
House (3 Bedrooms) | Interior

Charming Hampton Bays Home 5 Mi to Coopers Beach

3.0 star property
Charming Hampton Bays Home 5 Mi to Coopers Beach
Sabbatical a Private guest cottage in Sag Harbor
Exterior

Sabbatical a Private guest cottage in Sag Harbor

9.6 out of 10, Exceptional, (9)
"I can’t thank enough our hostess Susan for her amazing hospitality and kindness! I strongly recommend her place to stay for vacation!"
Sabbatical a Private guest cottage in Sag Harbor
1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.
Interior

1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.

10.0 out of 10, Exceptional, (1)
"Couldn’t have been easier. Full amenities, easy walk to town. 5stars"
1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.
Unique Southampton Getaway w/ Rooftop Deck!
House (3 Bedrooms) | Interior

Unique Southampton Getaway w/ Rooftop Deck!

3.0 star property
Unique Southampton Getaway w/ Rooftop Deck!
Hamptons Waterfront- Great Location!
On the beach, sun loungers, beach towels

Hamptons Waterfront- Great Location!

10.0 out of 10, Exceptional, (39)
"Super clean and great place on the water! I had so much fun with my friends staying here - we loved it and would recommend to anyone! Thank you for a great stay!"
Hamptons Waterfront- Great Location!
Hampton Bays Retreat: Walk to Squires Beach!
House (2 Bedrooms) | Interior

Hampton Bays Retreat: Walk to Squires Beach!

3.0 star property
6.0 out of 10, (1)
"Getting in and out of the property was very difficult. All the codes for the front door did not work and we were on the phone for an hour trying to get in. We had to go through the rental company as the owner didn’t answer any of our calls or texts. Also, locking the front door was very problematic. None of the shampoo, conditioner, or soap dispensers worked. The sheets were so itchy and horrible that we had to switch from the queen bed to the twin beds. Overall, the beds didn’t feel very clean...
Hampton Bays Retreat: Walk to Squires Beach!
Hamptons Vacation Rental w/ Seasonal Pool!
Fridge, microwave, stovetop, dishwasher

Hamptons Vacation Rental w/ Seasonal Pool!

10.0 out of 10, Exceptional, (5)
"My family enjoyed staying at this lovely property. The backyard was especially great! My kids splashed in the heated pool and jumped on the trampoline every day! The location was ideal and very close to the beach. We would definitely return. "
Hamptons Vacation Rental w/ Seasonal Pool!
Waterfront New York Getaway w/ Kayaks
Property grounds

Waterfront New York Getaway w/ Kayaks

Waterfront New York Getaway w/ Kayaks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Town of Southampton Hotel Reviews

Baron's Cove

Baron's Cove

10/10 Excellent
"Barons Cove Inn is very well located i.e. walkable to pretty much everything. It’s also charming, somewhat quirky, clean, comfortable, has very nice room amenities and internet access, a friendly attentive staff, a nice bar and restaurant, a lovely pool, is waterfront and has a great front porch with rockers. What’s not to like? We’ll definitely be making return visits. "
Christine 3-night trip
Posted 1 day ago
Baron's Cove