Photo by 4 Star Traveler

Search Vacation Homes in Riverhead

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Riverhead vacation homes

Smart TV, fireplace, table tennis, books
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
$6,469 nightly
The price is $7,391
Jan 5 - Jan 6, 2026
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Dining
3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (22)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
$546 nightly
The price is $624
Dec 30 - Dec 31
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,114 nightly
The price is $1,273
Jan 4 - Jan 5, 2026
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Smart TV, fireplace
Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
$5,705 nightly
The price is $6,518
Dec 29 - Dec 30
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Interior
Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
$5,596 nightly
The price is $6,393
Dec 27 - Dec 28
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
Property grounds
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
$1,504 nightly
The price is $1,593
Jan 5 - Jan 6, 2026
Total with taxes and fees
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Outdoor dining
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,113 nightly
The price is $1,272
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$240 nightly
The price is $274
Jan 8 - Jan 9, 2026
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Smart TV, books
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (23)
"Pet friendly "
United States
Steven
$463 nightly
The price is $529
Jan 1 - Jan 2, 2026
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Exterior detail
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
Calverton
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
$582 nightly
The price is $665
Dec 25 - Dec 26
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Interior
4-bedroom beach house minutes from Hamptons

4-bedroom beach house minutes from Hamptons

4-bedroom beach house minutes from Hamptons
2.0 star property
Calverton
$730 nightly
The price is $834
Jan 5 - Jan 6, 2026
Total with taxes and fees
4-bedroom beach house minutes from Hamptons
Fridge, microwave, oven, stovetop
Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
$520 nightly
The price is $594
Jan 2 - Jan 3, 2026
Total with taxes and fees
Modern Vacation home. Close to The Hamptons
Smart TV, fireplace
Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated
Greenport
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
$528 nightly
The price is $603
Dec 25 - Dec 26
Total with taxes and fees
Northfork Townhouse- walk to all/ newly renovated
Terrace/patio
Hottub, ⛳️, htd pool, Sauna, Basketball

Hottub, ⛳️, htd pool, Sauna, Basketball

Hottub, ⛳️, htd pool, Sauna, Basketball
Mastic
10.0 out of 10, Exceptional, (27)
"Excellent accommodations for a large family gathering.The home is inviting and comfortable. It offers many amenities and the host is very hospitable. "
United States
Maria C.
$1,611 nightly
The price is $1,841
Dec 30 - Dec 31
Total with taxes and fees
Hottub, ⛳️, htd pool, Sauna, Basketball
Dining
Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
$549 nightly
The price is $627
Dec 25 - Dec 26
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Living area
Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
$1,707 nightly
The price is $1,950
Dec 25 - Dec 26
Total with taxes and fees
Cozy 5 Bedroom With Wi-fi And Air Condition
Private kitchen
4-bedroom house in awesome Brookhaven with AC

4-bedroom house in awesome Brookhaven with AC

4-bedroom house in awesome Brookhaven with AC
Brookhaven
$640 nightly
The price is $731
Jan 15 - Jan 16, 2026
Total with taxes and fees
4-bedroom house in awesome Brookhaven with AC
Dining
Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all
Greenport
10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
$623 nightly
The price is $712
Dec 25 - Dec 26
Total with taxes and fees
Charming Northfork Townhouse- walk to all
Property grounds
Beachfront Greenport Villa

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (10)
"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!"
United States
Melissa F.
$777 nightly
The price is $888
Dec 25 - Dec 26
Total with taxes and fees
Beachfront Greenport Villa
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Riverhead Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Room was beautiful and spacious. Staff was courteous and on point. "
Ron 2-night trip
Posted 1 day ago
The Bentley Hotel Southampton

Find out more about Riverhead

Riverhead Vacation Homes information

Number of reviews
158
Accommodation
1412 Vacation Homes
Lowest Price
$274
Highest Price
$7,391

Explore a world of travel with Expedia