Search vacation rentals in Chesapeake Bay from 100+ sites!

9615 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chesapeake Bay vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Chesapeake Bay

Best Chesapeake Bay vacation rentals with a balcony

Rooftop Chesapeake Bay Views! Waterfront Retreat - Chesapeake Bay
No reviews

Rooftop Chesapeake Bay Views! Waterfront Retreat

apartment, Mathews
This Westville condo is located less than 15.5 miles from the Bay School Community Arts Center, Cobbs Creek Arts Center, Gwynn's Island Museum, Ware Parish Church, and the Fairfield Foundation.
This pet-friendly apartment offers a full kitchen with a microwave and dishwasher, air conditioning, a swimming pool, barbecue facilities, private balconies, and complimentary on-site parking.
Club Wyndham Kingsgate - Chesapeake Bay
8.9 4325 reviews

Club Wyndham Kingsgate

resort, Williamsburg
Club Wyndham Kingsgate is located in Williamsburg, just a short walk from the historic area, offering a tranquil escape amidst the colonial charm. This 3-star hotel receives very good user ratings for its comfortable accommodations and amenities.
The resort features a colonial-style design, creating a unique atmosphere. Guests can enjoy a variety of amenities, including a swimming pool, jacuzzi, fitness center, restaurant, bar, and tennis court.
El  Camino - Chesapeake Bay
10 59 reviews

El Camino

cabin, Piney Point
This Piney Point waterfront cottage is located less than a mile from Cardinal Gibbons Park and First District Community Park, and about 3 miles from Saint Inigoes State Forest, offering easy access to outdoor recreation. This one-bedroom, one-bathroom getaway sleeps three guests and features a fully equipped kitchen, Smart TV, barbecue grill, and a terrace with stunning water views.
Holiday Inn Hotel & Suites Gateway By Ihg - Chesapeake Bay
8.9 1367 reviews

Holiday Inn Hotel & Suites Gateway By Ihg

resort, Williamsburg
The Holiday Inn Hotel & Suites Gateway, An Ihg Hotel, is located in Williamsburg, just 2 miles from the College of William and Mary and the Colonial Williamsburg Historic Area. It has received a very good rating for cleanliness and user experience and an excellent rating for its location.
The hotel is designed for families and offers comfortable rooms with modern amenities. The hotel also features a fitness center, a pool, a restaurant, a bar, and a spa, providing guests with plenty of opportunities for relaxation and recreation.

Search Family Vacation Rentals in Chesapeake Bay

These family-friendly vacation rentals in Chesapeake Bay offer plenty of room to spread out near local beaches.

Old World Cottage/fabulous Sunsets/polite Pets Ok - Chesapeake Bay
9.8 132 reviews

Old World Cottage/fabulous Sunsets/polite Pets Ok

apartment, Tall Timbers
This cottage in St. Mary's County, Maryland, offers direct access to the Potomac River for sunset views and is a short walk to Tall Timbers Marina, with proximity to Piney Point and St. George's Island.
This pet-friendly, family-friendly rental accommodates up to eight guests with three bedrooms, a fully stocked kitchen, fast internet, Smart TVs, kayaks, and a crab net, featuring a large stone patio and a front-yard fire pit.
* Private Suite Full Of Style & Comfort * - Chesapeake Bay
9.0 48 reviews

* Private Suite Full Of Style & Comfort *

apartment, Lutherville
This apartment is perfect for travelers visiting Lutherville. It is located in the heart of Lutherville Timonium, within a 3-mile radius of Goucher College, Towson Town Center, and Towson University. The apartment has received excellent user ratings and can accommodate up to 4 guests with 1 bedroom and 1 bathroom.
The apartment features a fully equipped kitchen, a comfortable living space with a sofa bed, a Smart TV with a DVD player, a washing machine, and access to a garden. It is also pet-friendly and offers parking.
Guest Suite For Up To 2 In A Victorian On The Chester River - Chesapeake Bay
9.8 27 reviews

Guest Suite For Up To 2 In A Victorian On The Chester River

apartment, Millington
This Millington apartment rental boasts a riverside location, conveniently situated within six miles of Crumpton Park and Tilmon's Island Winery, and under nine miles from Pinkney Park and Chase Island.
The one-bedroom, one-bathroom unit sleeps two guests and includes free WiFi, a Smart TV, in-unit appliances (refrigerator, microwave, coffee/tea maker, hairdryer), on-site parking, and a playground.
Pint-sized On Poplar | Across The Street From Rar - Chesapeake Bay
10 21 reviews

Pint-sized On Poplar | Across The Street From Rar

apartment, Cambridge
This stylish loft is located in downtown Cambridge, directly across from RAR Brewing and above Night Kitchen Coffee Roasters, just steps from the Choptank waterfront and local attractions.
This one-bedroom, one-bathroom apartment accommodates two guests and features a full kitchen, in-unit washer and dryer, fast WiFi, a smart HDTV, and a rain head shower, offering a comfortable stay with direct access to downtown amenities.

Frequently Asked Questions about vacation rentals in Chesapeake Bay

  • Which neighborhood in Baie de Chesapeake should you consider for a vacation rental?

    If you're looking for a charming and historic area, consider staying in Annapolis. It's the state capital of Maryland and has a lot to offer, including great restaurants, shops, and attractions. You can also find some beautiful waterfront vacation rentals in Annapolis.
  • What are the best Airbnb and vacation rentals in Chesapeake Bay?

    Gem In The Heart Of The Fan #1, Lovely Large Room By River In "Kingsmill On The James" and Beautiful 1-bdrm Carytown - Fan - Vmfa are the most popular Airbnb and vacation rentals in Chesapeake Bay among travelers.

  • What are the top family-friendly attractions in Baie de Chesapeake?

    The Maryland Science Center in Baltimore is a great place for kids of all ages. They have interactive exhibits, a planetarium, and an IMAX theater. Also, the National Aquarium in Baltimore is a must-see, with a variety of marine life, including sharks, dolphins, and sea turtles.
  • What are the most popular Airbnbs in Chesapeake Bay?

  • When is the best time to book a vacation rental in Baie de Chesapeake?

    The best time to book a vacation rental in Chesapeake Bay is in the spring or fall. The weather is mild and the crowds are smaller. If you're looking for a beach vacation, you might want to book in the summer, but be prepared for higher prices and more crowds.
  • What are the best vacation rentals with a pool in Chesapeake Bay?

  • What events or festivals should visitors check out in and around Baie de Chesapeake?

    The Annapolis Maritime Museum hosts the annual Annapolis Boat Show in October. It's a great place to see all kinds of boats and talk to experts about boating. Also, the Chesapeake Bay Wine Festival in Stevensville is a great event to enjoy the local wines.
  • What are the best rentals for families and kids in Chesapeake Bay?

  • What are the best budget-friendly activities in Baie de Chesapeake?

    You can enjoy a beautiful walk or bike ride along the Bay Trail, which runs for miles along the shores of the Chesapeake Bay. You can also visit one of the many state parks in the area, like Sandy Point State Park, which offers hiking, fishing, and camping.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesapeake Bay?

  • What are the best restaurants with local dishes in Baie de Chesapeake?

    Try the Chesapeake Inn in Stevensville for their famous crab cakes. They're made with fresh, local crab meat and are a true taste of the Chesapeake Bay. You can also check out the Blackwall Hitch in Annapolis, which has a great selection of seafood and other Chesapeake Bay dishes.
  • What are the best walking or cycling routes in Baie de Chesapeake?

    The Bay Trail is a great option for walking or cycling. It runs for over 300 miles along the shores of the Chesapeake Bay, offering beautiful views and a chance to experience the natural beauty of the area. You can also find some great walking and cycling routes in the state parks, like Sandy Point State Park.
  • Are there pet-friendly attractions in Baie de Chesapeake?

    Many of the state parks in the area are pet-friendly, like Sandy Point State Park. You can also find many pet-friendly restaurants and shops in the area. Just be sure to check with individual businesses to see if they allow pets.
  • What are the benefits of choosing a vacation rental in Baie de Chesapeake?

    Vacation rentals offer more space and privacy than a hotel, and you can often find rentals that are pet-friendly. You can also find rentals in a variety of locations, from waterfront properties to those in the heart of town.

Popular destinations

Best Chesapeake Bay vacation rentals with parking

Large 4 Bedroom Walkable Restaurants Pets Welcome - Chesapeake Bay
9.3 36 reviews

Large 4 Bedroom Walkable Restaurants Pets Welcome

apartment, Kilmarnock
This spacious Reedville home, located on Main Street, offers easy walking access to the Reedville Fisherman's Museum, restaurants, and local shops.
The four-bedroom, two-bathroom house sleeps eight, includes a kitchen with a fridge, microwave, and dishwasher, plus air conditioning, parking, internet access, and a dedicated office space.
Salisbury Riverfront Lofts - Chesapeake Bay
9.4 26 reviews

Salisbury Riverfront Lofts

apartment, Salisbury
This Salisbury apartment is conveniently located near Peninsula Regional Medical Center and Poplar Hill Mansion, both within 1.2 miles.
The apartment offers a fully equipped kitchen, free Wi-Fi, a Smart TV with Netflix, and free on-site parking.
Private Annapolis Inlaw Apartment - Chesapeake Bay
9.8 366 reviews

Private Annapolis Inlaw Apartment

apartment, Annapolis
This Annapolis apartment is located in a quiet neighborhood just a short distance from the bustling downtown area, offering easy access to shops, restaurants, and historic attractions. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The apartment features a comfortable king-size bed, two queen-size blow-up beds, and a large sectional sofa, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, parking, and internet access for your convenience.
Cozy Fells Point Gem | In The Heart Of Fells Point - Chesapeake Bay
9.8 495 reviews

Cozy Fells Point Gem | In The Heart Of Fells Point

apartment, Baltimore
This smoke-free apartment is located in Fells Point, a historic waterfront district, within a mile of the Fell's Point Visitor Center and Johns Hopkins Hospital, and within two miles of the National Aquarium and Baltimore Inner Harbor Marina. It has excellent user, location, and cleanliness ratings.
The apartment has one bedroom and one bathroom, and it is 600 square feet. Guests can enjoy amenities such as a fully equipped kitchen, a comfortable living space with a Smart TV and internet access, and on-site parking.

Check Out Vacation Rentals with a Pool in Chesapeake Bay

A vacation rental with a pool in Chesapeake Bay is the ideal way to complement your daily coastal adventures.

Waterfront 4 Bedroom Home With Marina Facilities - Chesapeake Bay
9.6 63 reviews

Waterfront 4 Bedroom Home With Marina Facilities

apartment, Gloucester Point
This Gloucester Point home is a short drive from Busch Gardens and the Historic Colonial Triangle, offering easy access to area attractions while providing a peaceful setting. It consistently receives excellent ratings for location, cleanliness, and overall experience.
The home features four bedrooms and three bathrooms, comfortably accommodating up to eight guests. Guests can enjoy amenities like a swimming pool, garden, and private parking, as well as access to the Severn River for boating, fishing, and kayaking.
Oceanfront Resort Studio On Virginia Beach! - Chesapeake Bay
9.5 72 reviews

Oceanfront Resort Studio On Virginia Beach!

studio, Virginia Beach
This studio apartment sits directly on Virginia Beach, a short walk from Neptune's Park and a 2-mile drive to the Virginia Beach Fishing Pier. It has received excellent ratings for location, cleanliness, and overall user experience.
The studio features a private balcony with ocean views and a fully equipped kitchen. Guests can enjoy amenities like a swimming pool, spa, and parking, as well as access to the internet and a cable TV.
Pool Access! Cozy Couple's Getaway In Kilmarnock - Chesapeake Bay
10 1 review

Pool Access! Cozy Couple's Getaway In Kilmarnock

studio, Kilmarnock
This Kilmarnock apartment is located 53 miles from Newport News/Williamsburg International Airport.
This 500 square foot rental features air conditioning, Wi-Fi, and parking, accommodating up to 3 guests with a kitchen including a microwave and refrigerator.
Stylish Estate Stay Just Minutes From Museums, Dining & Attractions - Chesapeake Bay
No reviews

Stylish Estate Stay Just Minutes From Museums, Dining & Attractions

resort, Williamsburg
The "Stylish Estate Stay Just Minutes From Museums, Dining & Attractions" resort is located in Williamsburg, providing easy access to Busch Gardens, Colonial Williamsburg, and is a short drive from Newport News/Williamsburg Airport.
This family-friendly accommodation offers 603 sq. ft. rooms for up to 4 guests, featuring amenities such as an outdoor pool, fitness center, tennis, and miniature golf.

Find the Best Seaside Vacation Rentals in Chesapeake Bay

Relax near the shore in these coastal Chesapeake Bay vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.

Chesapeake Beach Charm: Cozy Home With Bay Views - Chesapeake Bay
9.7 75 reviews

Chesapeake Beach Charm: Cozy Home With Bay Views

apartment, Chesapeake Beach
Pet-friendly Smith Island Cottage W/ Golf Cart! - Chesapeake Bay
9.5 2 reviews

Pet-friendly Smith Island Cottage W/ Golf Cart!

house, Smith Island
1br Beachfront & Boardwalk Escape - Chesapeake Bay
No reviews

1br Beachfront & Boardwalk Escape

apartment, Virginia Beach
Peek-a-boo Water Views! Port Haywood Home W/ Yard - Chesapeake Bay
10 1 review

Peek-a-boo Water Views! Port Haywood Home W/ Yard

apartment, Mathews

Compare Luxury Vacation Rentals in Chesapeake Bay

Refined interiors and prime locations make these luxury waterfront vacation rentals in Chesapeake Bay the ideal choice for your stay.

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia - Chesapeake Bay
8.2 3004 reviews

Ocean Sands Resort, Oceanfront, Virginia Beach By Vacatia

resort, Virginia Beach

Discover Vacation Rentals with Saunas in Chesapeake Bay

Maximize your wellness with vacation rentals in Chesapeake Bay featuring on-site saunas and steam rooms.

️Charming Coastal/country Home W/3 Acres & Sauna!️ - Chesapeake Bay
9.8 405 reviews

️Charming Coastal/country Home W/3 Acres & Sauna!️

apartment, Stevensville
The Waterfront Retreat- With Sauna And Hot Tub! - Chesapeake Bay
10 2 reviews

The Waterfront Retreat- With Sauna And Hot Tub!

apartment, Tolchester
Squeaky Shores Gloucester, Va Waterfront York River Oasis - Chesapeake Bay
9.2 17 reviews

Squeaky Shores Gloucester, Va Waterfront York River Oasis

apartment, Gloucester Courthouse
Long Beach Wellness Retreat Sauna/hot Tub/cold Plunge - Chesapeake Bay
10 3 reviews

Long Beach Wellness Retreat Sauna/hot Tub/cold Plunge

apartment, Charlestown
©2026 cozycozy.com