Assawoman Rentals By Owner

There are a lot of options in Assawoman. If you plan on staying in the Assawoman area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Assawoman:

• PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds
• Waterfront 5 star: Ponies! SAVE! Off season Rates starting at 250.00
• The Brass Crab - Check in/out any day!
• Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator
• As close as you can get to the ocean south of Chincoteague
• Josie's Getaway - Pet Friendly -Mini-Vacations and Month to Monthly Available
• Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
• Waterfront Home - New Dock w/Boat Ramp - Pet Friendly - Reduced rate for 2026
• STUNNING WATERFRONT VIEWS!
• At the Water's Edge by Seaside Vacations & Sales

There are many large, family-friendly vacation homes available in Assawoman; however, here are the most popular family rentals listed on our site:

• Chincoteague Island Beach House - Sir Whelk-A-Lot - New! - Downtown Location! Bikes & Yaks Included!
• Blufin Bungalows & Marina
• Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACHn3 decks.
• ‘Beach Bay Pony Place’ w/Ponies: 1 Mi to Water!

Yes, there are 1092 self-catering vacation homes in Assawoman that have hot tubs, swimming pools, & other amenities.

There are more than 1092 luxury villas and vacation homes in or near Assawoman. Filter by price to compare find the most expensive places to stay on Whisperingpinescottages.

Yes, there are 1092 pet friendly vacation homes and places to stays that are available in or near Assawoman that you may consider.