Photo by Nina Dinoff

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
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Riverhead vacation homes

Property grounds
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, (21)
"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.
$543 nightly
The price is $620
Dec 10 - Dec 11
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!
Beach
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
$5,642 nightly
The price is $6,446
Dec 14 - Dec 15
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Outdoor pool, a heated pool
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.
$6,353 nightly
The price is $7,259
Dec 10 - Dec 11
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Outdoor dining
Port Jefferson Home Near Stony Brook University SBU

Port Jefferson Home Near Stony Brook University SBU

2.0 star property
Port Jefferson Station
$398 nightly
The price is $455
Dec 10 - Dec 11
Total with taxes and fees
Port Jefferson Home Near Stony Brook University SBU
Fridge, microwave, oven, stovetop
4-bedroom beach house minutes from Hamptons

4-bedroom beach house minutes from Hamptons

2.0 star property
Calverton
$583 nightly
The price is $666
Dec 14 - Dec 15
Total with taxes and fees
4-bedroom beach house minutes from Hamptons
Fridge, microwave, oven, stovetop
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
$473 nightly
The price is $540
Jan 1 - Jan 2, 2026
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
5 bedrooms, iron/ironing board, WiFi, bed sheets
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 12 - Dec 13
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
Beach
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Mastic Beach
10.0 out of 10, Exceptional, (5)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
United States
Leonid T.
$274 nightly
The price is $313
Dec 15 - Dec 16
Total with taxes and fees
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Outdoor spa tub
Hottub, ⛳️, htd pool, Sauna, Basketball

Hottub, ⛳️, htd pool, Sauna, Basketball

Mastic
10.0 out of 10, Exceptional, (27)
"Stayed here for my wedding weekends and absolutely loved the house! Very spacious and beautiful yard! Had so much fun "
United States
Tiffany I.
$971 nightly
The price is $1,109
Dec 10 - Dec 11
Total with taxes and fees
Hottub, ⛳️, htd pool, Sauna, Basketball
Oven, stovetop, dishwasher
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 10 - Dec 11
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Terrace/patio
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.
$242 nightly
The price is $277
Dec 10 - Dec 11
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Fridge, microwave, oven, stovetop
Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
$527 nightly
The price is $602
Dec 16 - Dec 17
Total with taxes and fees
Modern Vacation home. Close to The Hamptons
Terrace/patio
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
Outdoor pool
Pure Paradise Hamptons Getaway

Pure Paradise Hamptons Getaway

East Patchogue
10.0 out of 10, Exceptional, (1)
"Nice house and great pool. "
United States
Bret C.
Pure Paradise Hamptons Getaway
A heated 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)
"Just finished a 5 day stay. Best house rental ever! Great and thoughtful hosts. Super relaxing and extremely luxurious! Highly recommend!"
United States
William H.
$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,...
Private kitchen
Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition

Wainscott
$1,699 nightly
The price is $1,941
Dec 10 - Dec 11
Total with taxes and fees
Cozy 5 Bedroom With Wi-fi And Air Condition
Terrace/patio
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.
$562 nightly
The price is $642
Dec 10 - Dec 11
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Fridge, microwave, oven, stovetop
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.
$594 nightly
The price is $679
Dec 10 - Dec 11
Total with taxes and fees
Charming Northfork Townhouse- walk to all
Property grounds
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.
$914 nightly
The price is $1,044
Dec 10 - Dec 11
Total with taxes and fees
Beachfront Greenport Villa
Private kitchen
4-bedroom house in awesome Brookhaven with AC

4-bedroom house in awesome Brookhaven with AC

Brookhaven
$703 nightly
The price is $803
Jan 1 - Jan 2, 2026
Total with taxes and fees
4-bedroom house in awesome Brookhaven with AC
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 Preston House & Hotel

The Preston House & Hotel

10/10 Excellent
"The room was very spacious and nice and modern. It was beautiful. The staff was super helpful and nice also! "
Jennifer 1-night trip
Posted 2 days ago
The Preston House & Hotel

Find out more about Riverhead

Riverhead Vacation Homes information

Number of reviews
139
Accommodation
1412 Vacation Homes
Lowest Price
$277
Highest Price
$7,259

Explore a world of travel with Expedia