A bridge over calm water at sunset.

Cherry Grove Holiday Rentals

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Our top choices for Cherry Grove holiday rentals

1. Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is NZ$495
includes taxes & fees
7 Oct - 8 Oct
Sundown Escape-South Shore Long Island

2. Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood
9.4 out of 10, Exceptional, (52 reviews)
"This stay was very clean and easy. The check-in process was efficient. Thank you, I would definitely book again for a short stay!"
United States
Jaelyn
The price is NZ$291
includes taxes & fees
28 Sept - 29 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

3. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is NZ$591
includes taxes & fees
8 Oct - 9 Oct
Sundown Escape Near SouthShore University Hospital

4. Charming Secluded Waterfront retreat

Charming Secluded Waterfront retreat
Oakdale
The price is NZ$479
includes taxes & fees
8 Oct - 9 Oct
Charming Secluded Waterfront retreat

5. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (9 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is NZ$592
includes taxes & fees
5 Oct - 6 Oct
The Royal Suite - Ronkonkoma

6. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is NZ$560
includes taxes & fees
6 Oct - 7 Oct
Spacious 3BR Family Home Near Everything

7. Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
8.8 out of 10, Excellent, (8 reviews)
"He’s an excellent hosts and his place is well worth it."
United States
Rowena V.
The price is NZ$574
includes taxes & fees
6 Oct - 7 Oct
Peaceful private 2-bedroom house in Bayport. Amazing location!

8. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (25 reviews)
"Clean and friendly owners it’s in the side of there home but very peaceful no complaints "
United States
Matthew B.
The price is NZ$310
includes taxes & fees
8 Oct - 9 Oct
1 bedroom 1 bath private entrance

9. Fire Island Beach House Ocean Bay Park

Fire Island Beach House Ocean Bay Park
Ocean Beach
10.0 out of 10, Exceptional, (73 reviews)
"House was very big and spacious enough for our large group. The host was also very communicative and accommodating, would definitely love to come back and stay again."
United States
Mohit M.
The price is NZ$2,420
includes taxes & fees
27 Sept - 28 Sept
Fire Island Beach House Ocean Bay Park

10. Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
8.0 out of 10, Very good, (11 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is NZ$588
includes taxes & fees
6 Oct - 7 Oct
Spacious one Bedroom Apt with private entrance

11. Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
8.8 out of 10, Excellent, (3 reviews)
"My stay was amazing! The place was bigger in person than i expected, which was such a pleasant surprise. The house was spotless and very clean, making me feel comfortable from the moment I arrived. The host was incredibly helpful, responsive, and made the entire experience smooth and stress-free. I enjoyed my stay and would absolutely book this home again. Highly recommend to anyone looking for a clean, spacious, and welcoming place to stay!"
United States
Tatiana J.
The price is NZ$879
includes taxes & fees
29 Sept - 30 Sept
Bright & Comfortable Home in the Heart of It All

12. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (16 reviews)
"Love being able to park off the street."
United States
Joan
The price is NZ$396
includes taxes & fees
1 Oct - 2 Oct
Your Perfect Getaway Between Farmingdale & Amityville

13. Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach
Fire Island
9.8 out of 10, Exceptional, (7 reviews)
"Perfect Fire Island getaway. Great location and beautiful beach home. Would recommend and love to come back!"
United States
Jessica W.
The price is NZ$2,207
includes taxes & fees
8 Oct - 9 Oct
Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

14. Modern 2BR Retreat w/ Full Kitchen & Living

Modern 2BR Retreat w/ Full Kitchen & Living
Deer Park
6.0 out of 10, (2 reviews)
"Needs lots of repairs and cleaning.Didn’t understand how one room had two AC and two TV while the other room had none. I would liked to hang out on the porch but also not clean and there was no table but a couple dirty chairs."
United States
marlene D.
The price is NZ$603
includes taxes & fees
27 Sept - 28 Sept
Modern 2BR Retreat w/ Full Kitchen & Living

15. Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
9.4 out of 10, Exceptional, (30 reviews)
"The property was very easy to find, clean, and comfortable. The hosts were very communicative and accommodating. Highly recommend!"
United States
Karen D.
The price is NZ$316
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

16. Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (29 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is NZ$432
includes taxes & fees
26 Sept - 27 Sept
Private 1 bedroom apt in a quiet neighborhood, close to all!

17. 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, (24 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is NZ$1,086
includes taxes & fees
6 Oct - 7 Oct
3 Story Beach Waterview, 3 KING bed, golf putting green!

18. South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (6 reviews)
"Really nice and great price! Would stay again. "
United States
Philip P.
The price is NZ$398
includes taxes & fees
1 Oct - 2 Oct
South Shore Studio in Mastic

19. Private 3Br Apt: King-2Queen -PetPally -LTR-STR

Private 3Br Apt: King-2Queen -PetPally -LTR-STR
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"These were nice rooms. Very professionally set-up."
United States
Marcus P.
The price is NZ$737
includes taxes & fees
30 Sept - 1 Oct
Private 3Br Apt: King-2Queen -PetPally -LTR-STR

20. Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.4 out of 10, Exceptional, (8 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is NZ$472
includes taxes & fees
26 Sept - 27 Sept
Cozy king suite with kitchen and dining area.
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 Cherry Grove Hotel Reviews

Find out more about Cherry Grove

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cherry Grove holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cherry Grove. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cherry Grove. Seeing all the best attractions is bound to make you fall in love with Cherry Grove. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cherry Grove short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Cherry Grove?

Yes, there are holiday rentals in Cherry Grove close to Cherry Grove Community House and Theatre, or you can select a more secluded option if you're looking for a relaxing stay. Cherry Grove is known for its beaches.

What are some of the best holiday rentals that Cherry Grove has to offer?

Large Beach House Steps From Town and Ocean: This holiday home rental outside of Cherry Grove has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Cherry Grove?

Expedia has 8 holiday rentals for your stay in Cherry Grove.

What can I see and do in Cherry Grove?

Explore the area and family-friendly sights such as Bowl Long Island at Patchogue, or get out into nature at a spot like Ocean Beach. In the wider area, you’ll find Cherry Grove Community House and Theatre and Heckscher State Park.

What are holiday rentals like in Cherry Grove?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cherry Grove. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family trips.