Riverhead Holiday Rentals
House
10.0Exceptional
(28 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $462/Night
7 Nights - US $3,234
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
602.78 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
US $667/Night
7 Nights - US $4,669
Cottage
- New York
- ·
- Suffolk County
- 11.24 mi to center
1 Bedroom
1 Bath
Pool
Ocean View- Balcony/Terrace
- View
US $3,430/Night
7 Nights - US $24,007
Cottage
10.0Exceptional
(25 Reviews)
1 Bedroom
1 Bath
3 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $106/Night
7 Nights - US $742
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
548.96 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $592/Night
7 Nights - US $4,145
House
10.0Exceptional
(22 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
Hot Tub- Parking
- Ocean View
US $327/Night
7 Nights - US $2,291
Boat Rental
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $620/Night
7 Nights - US $4,339
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $232/Night
7 Nights - US $1,621
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
5 Guests
1435 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $560/Night
7 Nights - US $3,920
Luxury Holiday Rentals in Riverhead
Over 249+ Luxury Holiday Rentals in or Near Riverhead
House
- New York
- ·
- Suffolk County
- 19.21 mi to center
10.0Exceptional
(12 Reviews)
4 Bedrooms
3 Baths
8 Guests
4000 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $2,228/Night
7 Nights - US $15,593
House
- New York
- ·
- Suffolk County
- 20.90 mi to center
5 Bedrooms
6 Baths
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $2,218/Night
7 Nights - US $15,526
House
9.8Exceptional
(41 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,956/Night
7 Nights - US $13,692
House
10.0Exceptional
(7 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,892/Night
7 Nights - US $13,244
House
- New York
- ·
- Suffolk County
- 19.99 mi to center
4 Bedrooms
4 Baths
6 Guests
- Air Conditioner
Internet
Pet Friendly
Child Friendly
US $1,890/Night
7 Nights - US $13,227
House
- Riverhead
- ·
- South Jamesport
- 0.06 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,873/Night
7 Nights - US $13,108
Villa
- Riverhead
- ·
- Northville
- 0.69 mi to center
4 Bedrooms
4 Baths
10 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $1,722/Night
7 Nights - US $12,057
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
Private Pool- Parking
- Pool
- Balcony/Terrace
US $1,711/Night
7 Nights - US $11,980
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
3800 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,704/Night
7 Nights - US $11,930
Top-Rated Holiday Rentals with a Pool in Riverhead
Over 62+ The Best Private Villas and Holiday Rentals in Riverhead with a Pool
New
House
10.0Exceptional
(13 Reviews)
4 Bedrooms
1 Bath
8 Guests
1950 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,329/Night
7 Nights - US $9,301
House
- Riverhead
- ·
- Northville
- 1.51 mi to center
10.0Exceptional
(12 Reviews)
4 Bedrooms
3 Baths
8 Guests
2600 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $798/Night
7 Nights - US $5,587
House
- Riverhead
- ·
- Northville
- 1.82 mi to center
10.0Exceptional
(9 Reviews)
5 Bedrooms
3 Baths
12 Guests
3200 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,018/Night
7 Nights - US $7,128
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,502/Night
7 Nights - US $10,513
House
- New York
- ·
- Suffolk County
- 19.68 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $1,015/Night
7 Nights - US $7,102
House
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
9 Guests
2400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $833/Night
7 Nights - US $5,832
Hotel
9.8Exceptional
(437 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
US $470/Night
7 Nights - US $3,289
Apartment
9.4Exceptional
(6 Reviews)
1 Bedroom
1 Bath
3 Guests
475 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $259/Night
7 Nights - US $1,815
Hotel
9.2Exceptional
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $350/Night
7 Nights - US $2,447
Pet-Friendly Holiday Rentals in Riverhead
Over 78+ Pet-Friendly Holiday Rentals in or Near Riverhead
Cottage
9.8Exceptional
(19 Reviews)
2 Bedrooms
1 Bath
5 Guests
549 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $644/Night
7 Nights - US $4,510
Apartment
9.2Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1431.6 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $376/Night
7 Nights - US $2,631
Cottage
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
603 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $722/Night
7 Nights - US $5,053
House
2 Bedrooms
1 Bath
5 Guests
602.78 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $667/Night
7 Nights - US $4,669
Cottage
- Calverton
- ·
- Baiting Hollow
- 1.66 mi to center
9.6Exceptional
(5 Reviews)
1 Bedroom
1 Bath
5 Guests
750 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $357/Night
7 Nights - US $2,502
House
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $306/Night
7 Nights - US $2,139
House
- Riverhead
- ·
- Northville
- 0.53 mi to center
9.6Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $420/Night
7 Nights - US $2,939
House
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $796/Night
7 Nights - US $5,572
House
3 Bedrooms
1 Bath
6 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $525/Night
7 Nights - US $3,673
Large Holiday Rentals and Private Villas in Riverhead
Over 41+ Large Holiday Rentals and Private Villas in or Near Riverhead
House
- Calverton
- ·
- Baiting Hollow
- 0.85 mi to center
10.0Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $528/Night
7 Nights - US $3,695
Villa
- Calverton
- ·
- Baiting Hollow
- 0.50 mi to center
9.1Exceptional
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
398.26 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $393/Night
7 Nights - US $2,748
House
10.0Exceptional
(13 Reviews)
5 Bedrooms
3 Baths
8 Guests
2277 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $927/Night
7 Nights - US $6,489
House
8.5Fabulous
(7 Reviews)
5 Bedrooms
4 Baths
10 Guests
53.82 ft²
Private Beach- Parking
- Ocean View
- View
US $410/Night
7 Nights - US $2,867
House
10.0Exceptional
(9 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $877/Night
7 Nights - US $6,142
House
10.0Exceptional
(2 Reviews)
1 Bedroom
3 Baths
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,007/Night
7 Nights - US $7,049
House
10.0Exceptional
(1 Review)
6 Bedrooms
2 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,035/Night
7 Nights - US $7,243
House
9.6Exceptional
(29 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $979/Night
7 Nights - US $6,850
House
9.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
8 Guests
3300 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $756/Night
7 Nights - US $5,290
Wheelchair Accessible Holiday Homes in Riverhead
Over 16+ Wheelchair Accessible Holiday Homes in or Near Riverhead
Cottage
- Riverhead
- ·
- South Jamesport
- 0.18 mi to center
10.0Exceptional
(39 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Breakfast
- Parking
- Pool
- Ocean View
US $482/Night
7 Nights - US $3,374
Hotel
9.1Exceptional
(153 Reviews)
9 Baths
322.92 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $261/Night
7 Nights - US $1,829
Hotel
9.0Exceptional
(1000 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $338/Night
7 Nights - US $2,368
House
5.0Average
(36 Reviews)
4 Bedrooms
2 Baths
16 Guests
2400 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $857/Night
7 Nights - US $5,999
Hotel
9.0Exceptional
(275 Reviews)
1 Bath
259.68 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
US $329/Night
7 Nights - US $2,303
House
- Calverton
- ·
- Baiting Hollow
- 1.53 mi to center
4 Bedrooms
4 Baths
10 Guests
3203 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $359/Night
7 Nights - US $2,514
House
4.0Average
(3 Reviews)
1 Bedroom
2 Baths
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $125/Night
7 Nights - US $875
House
5.0Average
(1 Review)
3 Bedrooms
4 Baths
8 Guests
2300 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $950/Night
7 Nights - US $6,650
House
- New York
- ·
- Suffolk County
- 18.62 mi to center
1 Bedroom
1 Bath
2 Guests
215 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $689/Night
7 Nights - US $4,825
Riverhead Private Villas and Holiday Homes Under $200
Over 13+ Riverhead Private Villas and Holiday Homes Under $200
Apartment
- New York
- ·
- Suffolk County
- 8.93 mi to center
10.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
143 ft²
- Oceanfront
- Breakfast
EV Charge Station- Parking
US $136/Night
7 Nights - US $952
Hotel
7.2Very Good
(319 Reviews)
2 Baths
204.51 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $162/Night
7 Nights - US $1,132
Hotel
7.4Very Good
(822 Reviews)
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $159/Night
7 Nights - US $1,114
House
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Internet
- Child Friendly
US $150/Night
7 Nights - US $1,050
House
- Riverhead
- ·
- Northville
- 1.14 mi to center
9.8Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $133/Night
7 Nights - US $932
RV Rental
- Riverhead
- ·
- Northville
- 0.76 mi to center
8.4Excellent
(9 Reviews)
1 Bedroom
1 Bath
5 Guests
- Air Conditioner
- Child Friendly
Security/Safety
US $195/Night
7 Nights - US $1,365
Cottage
- Calverton
- ·
- Baiting Hollow
- 1.41 mi to center
4.2Average
(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Child Friendly
- Laundry
Bedding/Linens
US $120/Night
7 Nights - US $840
House
1 Bedroom
1 Bath
2 Guests
- Child Friendly
US $200/Night
7 Nights - US $1,400
House
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Bedding/Linens
US $180/Night
7 Nights - US $1,260
Instantly Bookable Holiday Homes in Riverhead
Over 83+ Instantly Bookable Holiday Homes in or Near Riverhead
Cottage
- Calverton
- ·
- Baiting Hollow
- 0.50 mi to center
9.8Exceptional
(47 Reviews)
1 Bedroom
1 Bath
4 Guests
400 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $462/Night
7 Nights - US $3,231
House
- Calverton
- ·
- Baiting Hollow
- 1.94 mi to center
4 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $1,867/Night
7 Nights - US $13,068
Cottage
- Calverton
- ·
- Baiting Hollow
- 0.61 mi to center
9.4Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $382/Night
7 Nights - US $2,675
Cottage
- Calverton
- ·
- Baiting Hollow
- 0.79 mi to center
2 Bedrooms
1 Bath
4 Guests
600 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $416/Night
7 Nights - US $2,911
Cottage
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $278/Night
7 Nights - US $1,949
Hotel
10.0Exceptional
(5 Reviews)
1 Bath
399 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $723/Night
7 Nights - US $5,063
Hotel
10.0Exceptional
(1 Review)
2 Baths
1129 ft²
- Breakfast
- Parking
- Ocean View
- Balcony/Terrace
US $867/Night
7 Nights - US $6,070
Hotel
9.0Exceptional
(2 Reviews)
1 Bath
399 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $749/Night
7 Nights - US $5,246
House
- Riverhead
- ·
- Northville
- 0.67 mi to center
10.0Exceptional
(58 Reviews)
3 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $495/Night
7 Nights - US $3,466
Book a Last Minute Place to Stay in Riverhead
About Casai's Private Villas and Holiday Rentals in Riverhead
Discover more than 258 vacation rentals available in Riverhead. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Riverhead.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Riverhead, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Riverhead. On average, places to stay near Riverhead offer 804.8 ft², with nightly prices averaging US $737.
With Casai, finding and comparing holiday rentals in Riverhead is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Riverhead
| Type | Count |
|---|---|
| Vacation Homes | 184 |
| Cottages | 30 |
| Holiday Apartments | 11 |
| Villas | 3 |
Use these Quick Filters to Find a Holiday Rental in Riverhead
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Riverhead.
Weather in Riverhead, NY
View the weather forecast for Riverhead before booking your Riverhead Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Riverhead, NY
Casai offers a large selection of top attractions around Riverhead . Research things to do on your vacation before you visit Riverhead.
Other Places to Stay in Riverhead, NY
Frequently Asked Questions About Riverhead?
What are the top holiday rentals in Riverhead?
With numerous options available in Riverhead, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Riverhead:
- Drifted Inn. North Fork Escape Paradise!
- Jamesport Cottage | Walk to Peconic Bay, Fire Pit
- Riverhead Farm House
- Wine Country Cozy Home Away in the Woods
- Hamptons Waterfront Suite Private Hot Tub Winter Escape Adults Only
- Peconic River Boatel
- Private Beach Retreat on Peconic Bay
- Modern Farmhouse Retreat North Fork Wine Country
- Recently Renovated and Re-Designed Vineyard Cottage Located on the 205 acre.
- Spacious Private Home Located on Palmer Vineyards in the North Fork,.
How many holiday rentals have private pools in Riverhead?
Discover a selection of holiday rentals with private pools near Riverhead with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- 2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub
- Hyatt Place Long Island East End
- North Fork Oasis w/Saltwater Pool & Steps 2 Beach
- Private property near beaches,wineries, close to everything
Which holiday homes in Riverhead are best for families?
If you're searching for a family-friendly holiday home in Riverhead, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Riverhead:
How many Casai.com holiday rentals are available in Riverhead?
As of 2026, Casai boasts over 258 properties listed in the Riverhead area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Riverhead.
People Also Ask
Map
