Holiday Rentals in Town of Southold Town

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Featured Holiday Rentals in Town of Southold Town

Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (235)
"Great location, great views. Walls are a little thin."
The price is €361
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
On the beach

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Another rental season is coming up.
Outdoor pool

Another rental season is coming up.

10.0 out of 10, Exceptional, (19)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.
American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is €315
includes taxes & fees
20 Aug - 21 Aug
American Beech in Greenport - Petite King Room 7
Beach, Pool, Wine, Shopping!
Beach nearby, beach towels

Beach, Pool, Wine, Shopping!

10.0 out of 10, Exceptional, (64)
"A great place. "
Beach, Pool, Wine, Shopping!
MATTITUCK, #1 Winery and Beach Town !
Fridge, microwave, oven, stovetop

MATTITUCK, #1 Winery and Beach Town !

10.0 out of 10, Exceptional, (104)
"The week went by fast and we enjoyed our time there. Beautiful home and landscaping to enjoy as well as great location to Hamptons."
MATTITUCK, #1 Winery and Beach Town !
The SandPiper
Terrace/patio

The SandPiper

9.8 out of 10, Exceptional, (24)
"My friends and I stayed here for a night after a wedding. It was the perfect place to stay after a long day. Host was kind and helpful with anything I needed! "
The SandPiper
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Terrace/patio

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (115)
"Lovely cottage on the Peconic Bay. We enjoyed our stay; found more than everything we needed. "
Lovely North Fork Beach Cottage (2 BR/2 bath)!
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Outdoor pool, a heated pool

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (3)
"The salt water pool was fantastic! We had a variety of family members from 1 year old to 60 years old and all enjoyed the property. Everything was neat, clean, and well maintained. We'll be back!"
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Beautifully farmhouse
Terrace/patio

Beautifully farmhouse

10.0 out of 10, Exceptional, (2)
"good experience"
The price is €1,026
includes taxes & fees
15 Sept - 16 Sept
Beautifully farmhouse
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
Outdoor spa tub

Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

10.0 out of 10, Exceptional, (178)
"The house and property were perfect for our group of friends to visit the north fork for a weekend. Lots of beds and bathrooms, and beautiful spacious indoor living area and kitchen. Outdoor space was wonderful! Deck, hot tub, firepit, osprey nest just across the water, front porch, and beach a short walk away. Southold is a great little town with lovely restaurants and the perfect central location for visiting wineries. Owners were great to work with, very quick to respond to messages. Loved it...
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Dining

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

9.4 out of 10, Exceptional, (9)
"What a lovely and peaceful location for a relaxing get away. This place checked all the boxes for us - right on the water (with kayaks and paddle boards to enjoy), fire pit in the sand right on the beach, heated pool (a bit finicky but we got the hang of the heating system), hot tub, nicely equipped kitchen, high quality linens and thoughtful touches throughout the home. Really nice stay!"
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
North Fork Beach House - short walk to Peconic Bay and beach
Property grounds

North Fork Beach House - short walk to Peconic Bay and beach

10.0 out of 10, Exceptional, (26)
"Wonderful house in an excellent location!"
North Fork Beach House - short walk to Peconic Bay and beach
Aqua Vista
Sun-loungers, beach towels

Aqua Vista

10.0 out of 10, Exceptional, (17)
"This was our second stay at Aqua Vista. We love the property. The house is recently renovated and everything is brand new. It is nicely decorated and very comfortable. It is located close to the beach and center of the town with all of the restaurants. The property manager is a great host. We enjoyed our visit to the fullest."
Aqua Vista
Escape to serene 3-bedroom Cutchogue haven with pool, near beaches & vineyards.
Terrace/patio

Escape to serene 3-bedroom Cutchogue haven with pool, near beaches & vineyards.

10.0 out of 10, Exceptional, (2)
"From booking to staying at this home was such an easy thing to do. The hosts were fantastic and the house was very comfortable and clean. All modern amenities in great shape and the pool was fantastic on a hot day. The hosts had pretty well everything you'll need for a great get away. This was a great way to catch up with a friend eat great food at the local restaurants, walk along some great beaches and then relax in the pool.We came from Australia and made a last minute booking so we could...
Escape to serene 3-bedroom Cutchogue haven with pool, near beaches & vineyards.
Spacious Beach House, Steps to Beach
Exterior detail

Spacious Beach House, Steps to Beach

10.0 out of 10, Exceptional, (18)
"Another wonderful stay at this beautiful home in Mattituck. The house has everything you need and the hosts are first rate. The perfect get away."
Spacious Beach House, Steps to Beach
Gorgeous Greenport Beach House right on the Sound! Breathtaking views
Interior

Gorgeous Greenport Beach House right on the Sound! Breathtaking views

9.8 out of 10, Exceptional, (6)
"We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!"
Gorgeous Greenport Beach House right on the Sound! Breathtaking views
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
Exterior

Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!

10.0 out of 10, Exceptional, (12)
"What a great little get away weekend in a beautiful cottage in the middle of wine country. Great host a lovely accommodations"
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI
Fridge, microwave, oven, stovetop

Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI

10.0 out of 10, Exceptional, (48)
"We were only out for two nights and could not have asked for a better find. We didn’t have to bring a single thing and could still walk into town easily!"
Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI
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.
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Top Town of Southold Town Hotel Reviews

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

10/10 Excellent
"Rented the cottage for my wife, 1.5 year old, and myself, Andrew was fantastic and easy to get in contact with for all questions/concerns. The cottage, grounds, pool, and hot tub are well maintained and we had a great experience overall. Will be planning another stay here! "
Robert L. 2-night trip
Posted 2 days ago
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day