A bridge over calm water at sunset.

Cherry Grove Vacation Rentals

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Our top choices for Cherry Grove vacation 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 CA $182
CA $414 total
includes taxes & fees
Aug 18 - Aug 19
Sundown Escape-South Shore Long Island

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

Fire Island-pines-historic House-heated Pool AND HOT TUB
Sayville
8.6 out of 10, Excellent, (12 reviews)
"Antoine was very responsive with any questions that we had. The pool was wonderful."
United States
Jodi F.
The price is CA $1,747
CA $2,743 total
includes taxes & fees
Aug 19 - Aug 20
Fire Island-pines-historic House-heated Pool AND HOT TUB

3. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is CA $200
CA $474 total
includes taxes & fees
Aug 18 - Aug 19
Sundown Escape Near SouthShore University Hospital

4. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is CA $233
CA $403 total
includes taxes & fees
Aug 18 - Aug 19
Spacious 3BR Family Home Near Everything

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

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
8.6 out of 10, Excellent, (7 reviews)
"Quiet and respectful owner. Welcoming and a great nights sleep. "
United States
Jason P.
The price is CA $437
CA $566 total
includes taxes & fees
Aug 24 - Aug 25
Peaceful private 2-bedroom house in Bayport. Amazing location!

6. 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, (49 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 $153
CA $246 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

7. 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 $3,538
CA $5,693 total
includes taxes & fees
Aug 27 - Aug 28
Oceanfront renovated home in FI Pines, stunning views & spacious outdoor oasis

8. 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 $1,109
CA $1,978 total
includes taxes & fees
Sep 1 - Sep 2
Fire Island Beach House Ocean Bay Park

9. 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 $273
CA $623 total
includes taxes & fees
Aug 25 - Aug 26
The Royal Suite - Ronkonkoma

10. Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer

Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer
Ronkonkoma
8.6 out of 10, Excellent, (7 reviews)
"Perfect stay and great communication!"
United States
Nick Y.
Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer

11. 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 $231
CA $676 total
includes taxes & fees
Sep 8 - Sep 9
Bright & Comfortable Home in the Heart of It All

12. 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 $156
CA $266 total
includes taxes & fees
Sep 3 - Sep 4
1 bedroom 1 bath private entrance

13. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
10.0 out of 10, Exceptional, (12 reviews)
"Love being able to park off the street."
United States
Joan
The price is CA $147
CA $297 total
includes taxes & fees
Aug 18 - Aug 19
Your Perfect Getaway Between Farmingdale & Amityville

14. 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 CA $328
CA $559 total
includes taxes & fees
Sep 8 - Sep 9
Private 3Br Apt: King-2Queen -PetPally -LTR-STR

15. 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 CA $187
CA $312 total
includes taxes & fees
Aug 18 - Aug 19
South Shore Studio in Mastic

16. 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 CA $156
CA $473 total
includes taxes & fees
Aug 18 - Aug 19
Spacious one Bedroom Apt with private entrance

17. 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 $169
CA $248 total
includes taxes & fees
Aug 18 - Aug 19
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

18. Waterfront house next to Bellport golf course

Waterfront house next to Bellport golf course
East Patchogue
10.0 out of 10, Exceptional, (17 reviews)
"Great house!"
United States
Eileen L.
The price is CA $1,103
CA $1,893 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront house next to Bellport golf course

19. Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.6 out of 10, Exceptional, (7 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is CA $243
CA $369 total
includes taxes & fees
Aug 19 - Aug 20
Cozy king suite with kitchen and dining area.

20. 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 CA $434
CA $1,108 total
includes taxes & fees
Sep 1 - Sep 2
3 Story Beach Waterview, 3 KING bed, golf putting green!
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 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?

5BR Retreat with Private Pool • Sleeps 15 • 20 Minutes to the Hamptons: Located near Cherry Grove, this vacation home rental offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a microwave, kitchenware, and a coffee maker, so you can cook with friends or family. You can relax into your vacation with a patio and a selection of games.

How many vacation rentals will I find in Cherry Grove?

Expedia has 8 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 Blydenburgh County Park, or get out into nature at a spot like Sunken Forest. 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.