Surfside Vacation Rental - Vacation Rentals in Assawoman

Chincoteague Bay RV Resort & Cottages From US $1,122
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Slack Tide by Seaside Vacations & Sales From US $319
         

9.8 (51 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Beach Pines by Seaside Vacations & Sales From US $281
         

9.4 (30 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

Luxury Places to Stay in Assawoman

Over 1258+ Luxury Places to Stay in or Near Assawoman
June's Retreat - Waterfront; Boat dock! From US $1,092
         

New
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Lookout on Main From US $906
         

New
House
  • Air Conditioner
  • Parking
  • View

Top-Rated Vacation Rentals with a Pool in Assawoman

Over 280+ Top-Rated Vacation Rentals with a Pool in or Near Assawoman
Chincoteague Island Getaway From US $758
         

10.0 (112 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Sunset Views on the Chincoteague Bay From US $455
         

10.0 (67 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Camping at its best From US $142
         

10.0 (22 Reviews)
RV Rental
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Assawoman

Over 358+ Pet-Friendly Vacation Rentals in or Near Assawoman
Historic Home Close to Main Street From US $197
         

9.6 (55 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Seahorse Shanty From US $396
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Blufin Bungalows & Marina From US $356
         

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9.6 (260 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
2BR Waterfront Cottage with the Most Spectacular View of lighthouse! From US $401
         

Ocean East 1 by Seaside Vacations & Sales From US $341
         

9.4 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Assawoman

Over 204+ Large Vacation Homes & Villas in or Near Assawoman
Beach House @ The Reef From US $172
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Belle Vue by Seaside Vacations & Sales From US $666
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Marsh Madness by Seaside Vacations & Sales From US $498
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sand Dollar Villa From US $313
         

10.0 (5 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
High Tide Hideaway by Seaside Vacations & Sales From US $292
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV

Wheelchair Accessible Vacation Homes in Assawoman

Over 63+ Wheelchair Accessible Vacation Homes in or Near Assawoman
Key West Cottages From US $520
         

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9.6 (393 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Comfort Suites Chincoteague Island Bayfront Resort From US $299
         

Sunset Bay 319 by Seaside Vacations & Sales From US $549
         

Sunset Bay 306 by Seaside Vacations & Sales From US $443
         

10.0 (6 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Assawoman Vacation Rentals and Airbnb Places to Stay Under $200

Over 210+ Assawoman Vacation Rentals and Airbnb Places to Stay Under $200
Sandpiper Retreat Chincoteague Island APT-A From US $135
         

9.8 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Chincoteague Island Cottage ~ 2 Mi to Beaches From US $170
         

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10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • View
Blue Pearl Cottage - Single Family Home- Screen Porch - NO LINENS PROVIDED From US $171
         

9.6 (54 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Island Time Cottage From US $155
         

10.0 (122 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Assawoman

Over 779+ Instantly Bookable Vacation Homes in or Near Assawoman
Calypso by Seaside Vacations & Sales From US $284
         

9.2 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
The C-Ray Cottage by Seaside Vacations & Sales From US $267
         

9.6 (23 Reviews)
House
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
Katydid - Water Front -3BR + loft home/Waterview LINENS & TOWELS PROVIDED From US $303
         

9.4 (39 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Blue Water - Single Family Home - In Town - LG. FENCEED IN YARD, NO LINENS From US $219
         

9.6 (20 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

About Assawoman Vacation Rentals

With more than 1267 Assawoman vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Surfsidevacationrental and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Assawoman.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Surfsidevacationrental Assawoman, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Assawoman. Places to stay near Assawoman are 539.08 ft² on average, with prices averaging US $333 a night.

Surfsidevacationrental makes it easy and safe to find and compare vacation rentals in Assawoman with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Assawoman

Type Count
Vacation Homes 1029
Cottages 59
Holiday Apartments 37
Hotels 36
Villas 14
Cabin Rentals 5
B&B 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Assawoman

Pro Tip: Surfsidevacationrental makes it easy to compare the best listings on Surfsidevacationrental homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Surfsidevacationrental 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 Assawoman.

Weather in Assawoman

View the weather forecast for Assawoman before booking your Assawoman 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

Assawoman Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Assawoman?
How many vacation rentals are available in Assawoman?

Currently, the total number of properties listed in 2026 is over 1267 in the Assawoman area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Assawoman.