A bridge over calm water at sunset.

Cherry Grove Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cherry Grove vacation rentals

1. 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, (48 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 CA $158
CA $252 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

2. 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 CA $168
CA $400 total
includes taxes & fees
Aug 6 - Aug 7
Sundown Escape-South Shore Long Island

3. Fire Island-pines-historic House-heated Pool AND HOT TUB

Fire Island-pines-historic House-heated Pool AND HOT TUB
Sayville
8.4 out of 10, Very good, (11 reviews)
"We loved our stay! The heated pool was perfect and we had everything we needed for a wonderful week in Fire Island Pines."
United States
Brian P.
The price is CA $1,768
CA $2,855 total
includes taxes & fees
Aug 19 - Aug 20
Fire Island-pines-historic House-heated Pool AND HOT TUB

4. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (8 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is CA $168
CA $491 total
includes taxes & fees
Aug 26 - Aug 27
The Royal Suite - Ronkonkoma

5. Beautiful Fire Island Pines Beach House—Pool, Hot Tub, Rooftop, Garden & More!

Beautiful Fire Island Pines Beach House—Pool, Hot Tub, Rooftop, Garden & More!
Sayville
9.6 out of 10, Exceptional, (7 reviews)
"Wonderful property and host. Host was very responsive any time we needed anything. Property very well represented on listing. The upper deck to lay out is especially nice and sunny all day long."
United States
Nicholas G.
The price is CA $1,403
CA $2,746 total
includes taxes & fees
Aug 6 - Aug 7
Beautiful Fire Island Pines Beach House—Pool, Hot Tub, Rooftop, Garden & More!

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

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
9.4 out of 10, Exceptional, (6 reviews)
"Quiet and respectful owner. Welcoming and a great nights sleep. "
United States
Jason P.
The price is CA $567
CA $738 total
includes taxes & fees
Aug 3 - Aug 4
Peaceful private 2-bedroom house in Bayport. Amazing location!

7. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (25 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is CA $164
CA $277 total
includes taxes & fees
Aug 3 - Aug 4
1 bedroom 1 bath private entrance

8. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is CA $202
CA $480 total
includes taxes & fees
Aug 12 - Aug 13
Sundown Escape Near SouthShore University Hospital

9. Oceanfront renovated home in FI Pines, stunning views & spacious outdoor oasis

Oceanfront renovated home in FI Pines, stunning views & spacious outdoor oasis
Fire Island Pines
10.0 out of 10, Exceptional, (3 reviews)
"An absolutely beautiful property! Stephen was very communicative throughout the entire stay and was an excellent host! Highly recommend staying here!"
United States
Sam D.
The price is CA $3,571
CA $5,794 total
includes taxes & fees
Aug 27 - Aug 28
Oceanfront renovated home in FI Pines, stunning views & spacious outdoor oasis

10. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is CA $294
CA $475 total
includes taxes & fees
Aug 12 - Aug 13
Spacious 3BR Family Home Near Everything

11. Private Apartment on River Ave. close to main st

Private Apartment on River Ave. close to main st
Patchogue
9.2 out of 10, Wonderful, (5 reviews)
"Nice little property. Perfect for what we needed. Host was great."
United States
A H.
The price is CA $418
CA $730 total
includes taxes & fees
Aug 7 - Aug 8
Private Apartment on River Ave. close to main st

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

Bright & Comfortable Home in the Heart of It All
Central Islip
10.0 out of 10, Exceptional, (2 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 CA $265
CA $724 total
includes taxes & fees
Aug 24 - Aug 25
Bright & Comfortable Home in the Heart of It All

13. Fire Island Beach House Ocean Bay Park

Fire Island Beach House Ocean Bay Park
Ocean Beach
10.0 out of 10, Exceptional, (72 reviews)
"Very nice place for a family to stay"
United States
James K.
The price is CA $1,259
CA $2,192 total
includes taxes & fees
Aug 31 - Sep 1
Fire Island Beach House Ocean Bay Park

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is CA $189
CA $272 total
includes taxes & fees
Aug 19 - Aug 20
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

15. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (10 reviews)
"Love being able to park off the street."
United States
Joan
The price is CA $149
CA $300 total
includes taxes & fees
Aug 12 - Aug 13
Your Perfect Getaway Between Farmingdale & Amityville

16. South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (5 reviews)
"Really nice and great price! Would stay again. "
United States
Philip P.
The price is CA $189
CA $317 total
includes taxes & fees
Aug 17 - Aug 18
South Shore Studio in Mastic

17. Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is CA $231
CA $753 total
includes taxes & fees
Aug 3 - Aug 4
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

18. Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
The price is CA $158
CA $481 total
includes taxes & fees
Aug 13 - Aug 14
Spacious one Bedroom Apt with private entrance

19. 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, (28 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 CA $217
CA $377 total
includes taxes & fees
Aug 11 - Aug 12
Private 1 bedroom apt in a quiet neighborhood, close to all!

20. 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.
Private 3Br Apt: King-2Queen -PetPally -LTR-STR
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cherry Grove Hotel Reviews

Find out more about Cherry Grove

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Cherry Grove?

Yes, we give you a choice of vacation rentals in Cherry Grove close to Cherry Grove Community House and Theatre, or you can select a more secluded option if you'd like a relaxing place to stay. Cherry Grove is known for its beaches.

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

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This vacation home rental near Cherry Grove has air-conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals will I find in Cherry Grove?

Expedia has 9 vacation 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 Bay Shore Mini Golf, or get out into nature at a spot like Sailors' Haven. In the larger area, you’ll find Cherry Grove Community House and Theatre and Carrington House.

What are vacation rentals like in Cherry Grove?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Cherry Grove. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.