Marthas Vineyard Cottages - Vacation Rentals in HealthSure

The Sweet Escape-25mi drive to "The Hamptons" From US $9,287
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Fancy Studio Private Entrance From US $116
         

|
9.6 (53 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Holiday Inn Long Island-Islip Arpt East by IHG From US $126
         

|
9.2 (947 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
3BR Home fully renovated in Medford From US $617
         

New
Villa
  • Air Conditioner
  • Security/Safety
  • Child Friendly
Hampton Inn Long Island-Brookhaven From US $135
         

|
8.8 (1378 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott Long Island Holtsville From US $154
         

|
8.8 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Cozy Manor of Farmingville From US $602
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Vacation home in Medford From US $184
         

New
House
  • Air Conditioner
  • Parking
  • Internet
Fairfield Inn by Marriott Medford Long Island From US $133
         

|
8.6 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn - Long Island - ISLIP Arpt East by IHG From US $148
         

|
8.8 (707 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Comfort Inn Medford - Long Island From US $125
         

8.4 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Soothing 3-bedroom apartment with AC in Farmingville From US $159
         

Hampton Inn Long Island-Brookhaven From US $198
         

|
8.6 (435 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Guest Suite W/BOAT RENTAL and Backyard! From US $444
         

8.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 1-bedroom apartment on Long Island, close to the beaches From US $168
         

LoversLane From US $146
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy Apartment in Farmingville From US $130
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Cozy and Spacious King size bedroom From US $75
         

5.0 (1 Review)
Other
  • Air Conditioner
  • TV
  • Bedding/Linens
Pro Tip: Marthasvineyardcottages makes it easy to compare the best listings on Marthasvineyardcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Marthasvineyardcottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in HealthSure.

Weather in HealthSure

View the weather forecast for HealthSure before booking your HealthSure 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

HealthSure Vacation Rental Frequently Asked Questions

How many vacation rentals are available in HealthSure?

Currently, the total number of properties listed in 2026 is over 30 in the HealthSure area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in HealthSure.