Search Vacation Homes in Chesapeake Bay

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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 602 Vacation Homes in Chesapeake Bay with updated reviews, rates, and availability.

Blufin Bungalows & Marina
On the beach

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (127)
"Excellent stay."
Blufin Bungalows & Marina
Capitol Hill & Eastern Market beauty w/ parking
Fridge, microwave, oven, stovetop

Capitol Hill & Eastern Market beauty w/ parking

10.0 out of 10, Exceptional, (81)
"Very convenient!"
The price is AED 580
AED 1,059 total
includes taxes & fees
8 Jun - 9 Jun
Capitol Hill & Eastern Market beauty w/ parking
3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Outdoor dining

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

2.0 star property
10.0 out of 10, Exceptional, (20)
"The unit was great. "
3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (218)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
House on the Gwynns Falls
Outdoor dining

House on the Gwynns Falls

9.0 out of 10, Wonderful, (15)
"Mary was great to deal with, very accommodating, and happily welcomed our dog. It was super convenient when visiting dear friends nearby."
The price is AED 621
AED 942 total
includes taxes & fees
12 Jun - 13 Jun
House on the Gwynns Falls
Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly
Exterior

Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly

9.8 out of 10, Exceptional, (9)
The price is AED 643
AED 1,704 total
includes taxes & fees
2 Jun - 3 Jun
Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly
Affordable Luxury Town Home in Federal Hill Baltimore.
Fridge, microwave, oven, stovetop

Affordable Luxury Town Home in Federal Hill Baltimore.

9.6 out of 10, Exceptional, (43)
"Our 4th time at this property. Manager is responsive and accommodating. The home is comfortable, clean and well appointed. Excellent location in safe, walkable neighborhood. Free street parking. Highly recommend. "
Affordable Luxury Town Home in Federal Hill Baltimore.
Cozy Vintage Escape – 4BR/4BA Near DC Attractions!
Desk, iron/ironing board, travel crib, free WiFi

Cozy Vintage Escape – 4BR/4BA Near DC Attractions!

10.0 out of 10, Exceptional, (1)
"Convenient location, good room separation, comfy beds and pillows "
Cozy Vintage Escape – 4BR/4BA Near DC Attractions!
Cape Charles home with pool and golf cart 5 minutes from the beach!
Miscellaneous

Cape Charles home with pool and golf cart 5 minutes from the beach!

9.6 out of 10, Exceptional, (7)
"Wedding in cape Charles va."
Cape Charles home with pool and golf cart 5 minutes from the beach!
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
On the beach

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

8.8 out of 10, Excellent, (56)
"Great stay "
The price is AED 1,098
AED 1,785 total
includes taxes & fees
16 Jun - 17 Jun
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
5 minutes from Washington DC 3 bedrooms 2 bath single family home with driveway
Fridge, microwave, oven, stovetop

5 minutes from Washington DC 3 bedrooms 2 bath single family home with driveway

10.0 out of 10, Exceptional, (1)
"Amazing stay! Very comfortable and convenient stay. Near local shopping area and Downtown, DC. Very resourceful amenties, appliances etc. Host communication was very prompt and effective. Definitely a highly recommended stay if looking to book in the area. I will definitely be booking this stay again in the near future! "
The price is AED 764
AED 1,698 total
includes taxes & fees
2 Jun - 3 Jun
5 minutes from Washington DC 3 bedrooms 2 bath single family home with driveway
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Parking

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is AED 3,276
AED 5,217 total
includes taxes & fees
10 Jun - 11 Jun
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Modern 2bd Getaway Walk to Metro Free Parking
Fridge, microwave, oven, stovetop

Modern 2bd Getaway Walk to Metro Free Parking

9.6 out of 10, Exceptional, (16)
"Very clean responsive host"
Modern 2bd Getaway Walk to Metro Free Parking
Serenity on the Bay-Complimentary Sunrise & Sunset Views
4 bedrooms, WiFi, bed sheets

Serenity on the Bay-Complimentary Sunrise & Sunset Views

9.6 out of 10, Exceptional, (35)
"The house sits on a beautiful bay, close to everything you need. Neat and tidy and the host Sony was communicative and easy to get ahold of."
Serenity on the Bay-Complimentary Sunrise & Sunset Views
Spacious Home w/Free Parking-Close to Old-town Alexandria and DC!
Smart TV, fireplace, computer monitors

Spacious Home w/Free Parking-Close to Old-town Alexandria and DC!

9.8 out of 10, Exceptional, (23)
"Really enjoyed the rental property. Would rent it again!"
The price is AED 1,194
AED 1,523 total
includes taxes & fees
10 Jun - 11 Jun
Spacious Home w/Free Parking-Close to Old-town Alexandria and DC!
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
On the beach, sun loungers

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

9.0 out of 10, Wonderful, (61)
"We had a great time"
The price is AED 988
AED 1,650 total
includes taxes & fees
4 Jun - 5 Jun
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Terrace/patio

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

10.0 out of 10, Exceptional, (1)
"Wonderful property!! My family and I had a great time. The location is very convenient to about everything. "
The price is AED 1,465
AED 2,528 total
includes taxes & fees
1 Jun - 2 Jun
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Quaint 3/2.5 home in Fort Dupont
Private kitchen

Quaint 3/2.5 home in Fort Dupont

8.0 out of 10, Very Good, (16)
"Nice place and a good location not far from downtown"
The price is AED 411
AED 1,134 total
includes taxes & fees
3 Jun - 4 Jun
Quaint 3/2.5 home in Fort Dupont
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Fridge, microwave, oven, stovetop

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (48)
"Adorable spot, walkable to all the island favorites."
The price is AED 459
AED 1,110 total
includes taxes & fees
2 Jun - 3 Jun
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Perfect for Families that Want to be Close to DC
Dining

Perfect for Families that Want to be Close to DC

10.0 out of 10, Exceptional, (51)
"Great location and extremely accommodating host. Highly recommend this home. "
Perfect for Families that Want to be Close to DC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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