Hawaii Wedding Travel - Vacation Rentals in Oyster Harbor

Chesapeake Bay single family home From US $597
         

9.6 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Oasis by the Bay - Waterfront Heated Pool Hot Tub From US $955
         

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10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Annapolis WaterVIEW Home From US $562
         

9.8 (58 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Yellow Cottage on Harness Creek From US $307
         

10.0 (170 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Eastport Cottage .5 mi from Downtown Annapolisnn From US $420
         

Luxury Places to Stay in Oyster Harbor

Over 218+ Luxury Places to Stay in or Near Oyster Harbor
Nantucket on the Chesapeake Heated Pool From US $2,879
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Annapolis Bayfront Home From US $1,531
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Oyster Harbor

Over 28+ Top-Rated Vacation Rentals with a Pool in or Near Oyster Harbor
Stunning Waterfront Cottage with Breathtaking Views! From US $449
         

10.0 (220 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Boat-N-Breakfast! Luxurious Accommodations Aboard a 44' Catamaran From US $484
         

Oasis by the Bay - Waterfront Heated Pool Hot Tub! From US $888
         

8.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Admiral's Retreat From US $1,200
         

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7.0 (1 Review)
House
  • Air Conditioner
  • Pool
  • View

Pet-Friendly Vacation Rentals in Oyster Harbor

Over 65+ Pet-Friendly Vacation Rentals in or Near Oyster Harbor
Water Views - Close to Downtown Annapolis From US $528
         

10.0 (46 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bella Chateau From US $914
         

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9.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Charming Annapolis WaterVIEW Home From US $896
         

9.6 (51 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026 From US $498
         

Annapolis Home Near Beach & Quiet Waters Park! From US $508
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026 From US $568
         

Large Vacation Homes & Villas in Oyster Harbor

Over 60+ Large Vacation Homes & Villas in or Near Oyster Harbor
The Salty Crab From US $419
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • View
  • Ocean View
Pet-Friendly & Spacious Home in Annapolis From US $537
         

Brand New Spacious Luxury Home From US $696
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Oyster Harbor

Over 2+ Wheelchair Accessible Vacation Homes in or Near Oyster Harbor

Oyster Harbor Varoom and Airbnb Places to Stay Under $200

Over 13+ Oyster Harbor Varoom and Airbnb Places to Stay Under $200
Water view studio. 20 minutes from Annapolis. From US $179
         

Private Apartment - Minutes to USNA From US $152
         

10.0 (17 Reviews)
House
  • Security/Safety
  • Barbecue/Outdoor Cooking
  • Child Friendly
Charming Eastport From US $119
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Private 2 BR Apt -- Less than 1 mi to Downtown & USNA gate From US $145
         

4.9 (14 Reviews)
Apartment
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly

Instantly Bookable Vacation Homes in Oyster Harbor

Over 87+ Instantly Bookable Vacation Homes in or Near Oyster Harbor
Searenity Stays, a Cozy Home From US $219
         

10.0 (39 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Private Cottage on gated estate From US $242
         

10.0 (32 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Oyster Harbor Vacation Rentals

With more than 227 Oyster Harbor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hawaiiweddingtravel 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 Oyster Harbor.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hawaiiweddingtravel Oyster Harbor, 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 Oyster Harbor. Places to stay near Oyster Harbor are 1188.2 ft² on average, with prices averaging $634 a night.

Hawaiiweddingtravel makes it easy and safe to find and compare vacation rentals in Oyster Harbor 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 Oyster Harbor

Type Count
Vacation Homes 183
Holiday Apartments 20
Cottages 12
B&B 1

Use these Quick Filters to Find a Vacation Rental in Oyster Harbor

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

Weather in Oyster Harbor

View the weather forecast for Oyster Harbor before booking your Oyster Harbor 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