Chesapeake Bay Vacation Rentals - Wimdu base64Hash Chesapeake Bay Vacation Rentals - Wimdu

Chesapeake Bay Vacation Rentals

Anytime
Guests
Anytime
Guests
Choose from 9,880 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chesapeake Bay

Discover vacation rentals with top-notch guest ratings

House Annapolis
from $1,466 per night
House ∙ 14 guests ∙ 6 bedrooms

Family-oriented beautiful vacation home with private pool, barbeque & patio | Perfect for remote work | Dogs allowed

5.0
Outstanding(40 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Cape Charles
from $445 per night
House ∙ 12 guests ∙ 4 bedrooms

House with BBQ, pool & garden | City view

5.0
Outstanding(22 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal
House Port Republic
from $217 per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented pleasant house with terrace & grill

5.0
Outstanding(22 ratings)
Port Republic, Solomons Island, Maryland, United States
View deal

Pet-friendly rentals in Chesapeake Bay

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

House Cape Charles
from $275 per night
House ∙ 10 guests ∙ 1 bedroom

Children-friendly house with pool, yard & patio | Good for workation | Pets allowed

4.8
Outstanding(18 ratings)
Cape Charles, Northampton County, Virginia, United States
Pet-friendly
View deal
Cabin Northeast Virginia Beach
from $164 per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Nice cottage | Next to the beach | Pets are welcome

5.0
Outstanding(6 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Pet-friendly
View deal
Houseboat Havre de Grace
from $247 per night
Houseboat ∙ 10 guests ∙ 4 bedrooms

Children-friendly beautiful boat with terrace & BBQ | Pets are welcome

4.8
Outstanding(53 ratings)
Havre de Grace, Harford County, Maryland, United States
Pet-friendly
View deal
See all pet-friendly offers

Vacation rentals with pool in Chesapeake Bay

Discover best cabin and house rentals with pool in Chesapeake Bay

House Reedville
from $1,033 per night
House ∙ 18 guests ∙ 8 bedrooms

Vacation home with patio, garden & heated pool | Nature view

5.0
Outstanding(91 ratings)
Reedville, Northumberland County, Virginia, United States
Pool
View deal
Condo Northeast Virginia Beach
from $145 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool & barbeque | Beach view

4.7
Excellent(34 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Pool
View deal
House Cape Charles
from $561 per night
House ∙ 11 guests ∙ 4 bedrooms

Family-friendly beautiful house with private pool, barbecue & garden | City view | Perfect for remote work

5.0
Outstanding(23 ratings)
Cape Charles, Northampton County, Virginia, United States
Pool
View deal
See all offers with pool

Best vacation rental offers in Chesapeake Bay

House Scotland
from $752 per night
House ∙ 14 guests ∙ 7 bedrooms

House with terrace, barbecue & garden | Nature view | Good for workation

5.0
Outstanding(32 ratings)
Scotland, St. Inigoes, Maryland, United States
View deal
House Chesapeake City
from $750 per night
House ∙ 15 guests ∙ 7 bedrooms

House with BBQ, terrace & jacuzzi

5.0
Outstanding(69 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
House Chesapeake Ranch Estates-Drum Point
from $250 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped charming vacation home with patio & barbeque | Beach nearby

4.8
Outstanding(18 ratings)
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
View deal
House Chesapeake Ranch Estates-Drum Point
from $290 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped vacation home with barbecue & terrace

5.0
Outstanding(118 ratings)
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
View deal
House Reedville
from $210 per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented vacation home with barbeque

5.0
Outstanding(9 ratings)
Reedville, Northumberland County, Virginia, United States
View deal
House Broad Creek
from $248 per night
House ∙ 8 guests ∙ 4 bedrooms

House with garden, sauna & barbecue | Suitable for remote work

3.1
(25 ratings)
Broad Creek, Norfolk, Virginia, United States
View deal
House Northeast Virginia Beach
from $217 per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with grill

5.0
Outstanding(9 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
House Accomack County
from $291 per night
House ∙ 16 guests ∙ 5 bedrooms

Child-friendly pleasant vacation home with barbecue & terrace | Good for workation | Pet-friendly

5.0
Outstanding(4 ratings)
Accomack County, Virginia, United States
View deal
House Fox Hill - Grandview
from $577 per night
House ∙ 12 guests ∙ 4 bedrooms

Children-friendly vacation home with barbeque, private pool & hot tub | Beach nearby

4.6
Excellent(77 ratings)
Fox Hill - Grandview, Hampton, Virginia, United States
View deal
House Northwest
from $197 per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented vacation home with patio | Close to the beach | Good for workation

4.8
Outstanding(93 ratings)
Northwest, Virginia Beach, Virginia, United States
View deal
House Cobbs Creek
from $150 per night
House ∙ 6 guests ∙ 3 bedrooms

House with grill, yard & pool | Nature view

4.9
Outstanding(185 ratings)
Cobbs Creek, Piankatank, Virginia, United States
View deal
House Northeast Virginia Beach
from $256 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped big vacation home with patio, jacuzzi & BBQ | Beach nearby | Dogs allowed

Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
Cabin Luttrels Corner
from $182 per night
Cabin ∙ 5 guests ∙ 3 bedrooms

Family-friendly ample cottage with BBQ & yard | Good for workation | Pets are welcome

5.0
Outstanding(45 ratings)
Luttrels Corner, Northumberland County, Virginia, United States
View deal
House Dorchester County
from $1,080 per night
House ∙ 16 guests ∙ 6 bedrooms

Child-friendly lovely vacation home with garden, patio & heated pool | Dogs allowed

5.0
Outstanding(2 ratings)
Dorchester County, Maryland, United States
View deal
House Cape Charles
from $343 per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, pool & garden

5.0
Outstanding(26 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal
House Madison
from $1,446 per night
House ∙ 24 guests ∙ 10 bedrooms

House with terrace, garden & private pool | Good for workation

5.0
Outstanding(81 ratings)
Madison, Dorchester County, Maryland, United States
View deal
House Shady Side
from $749 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with barbeque, patio & garden | Nature view | Perfect for remote work

5.0
Outstanding(9 ratings)
Shady Side, Anne Arundel County, Maryland, United States
View deal
House Northeast Virginia Beach
from $567 per night
House ∙ 9 guests ∙ 4 bedrooms

Child-friendly vacation home with yard, barbeque & patio | Close to the beach

4.9
Outstanding(23 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
House Willoughby Spit
from $437 per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly wonderful house with barbecue, garden & terrace | Pets allowed

5.0
Outstanding(19 ratings)
Willoughby Spit, Norfolk, Virginia, United States
View deal
House Norfolk
from $148 per night
House ∙ 6 guests ∙ 4 bedrooms

Family-oriented pleasant house | Pet-friendly

4.7
Excellent(31 ratings)
Norfolk, Virginia, United States
View deal
House Dam Neck
from $611 per night
House ∙ 13 guests ∙ 5 bedrooms

Family-friendly pleasant vacation home with jacuzzi, yard & barbeque | Nature view | Close to the beach | Perfect for remote work | Dogs allowed

3.9
Good(147 ratings)
Dam Neck, Virginia Beach, Virginia, United States
View deal
House Cape Charles
from $316 per night
House ∙ 10 guests ∙ 3 bedrooms

Child-friendly vacation home with private pool, terrace & yard | Nature view

5.0
Outstanding(52 ratings)
Cape Charles, Northampton County, Virginia, United States
View deal
House Cambridge
from $602 per night
House ∙ 16 guests ∙ 5 bedrooms

Children-friendly pleasant house with terrace, private pool & grill

5.0
Outstanding(48 ratings)
Cambridge, Dorchester County, Maryland, United States
View deal
House Virginia Beach
from $326 per night
House ∙ 12 guests ∙ 4 bedrooms

Child-friendly spacious vacation home with barbecue, yard & terrace | Good for workation | Pets are welcome

4.9
Outstanding(231 ratings)
Virginia Beach, Virginia, United States
View deal
Condo Northeast Virginia Beach
from $117 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-oriented condo with private pool & terrace | Nature view | Close to the beach

4.7
Excellent(200 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
View deal
Cabin Deal Island
from $255 per night
Cabin ∙ 9 guests ∙ 3 bedrooms

Cottage with terrace & grill | Suitable for remote work

4.9
Outstanding(19 ratings)
Deal Island, Somerset County, Maryland, United States
View deal
House Kilmarnock
from $407 per night
House ∙ 13 guests ∙ 6 bedrooms

Family-friendly vacation home with patio, barbeque & yard

4.8
Outstanding(30 ratings)
Kilmarnock, Lancaster County, Virginia, United States
View deal
Cabin Port Republic
from $145 per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cabin with terrace, yard & pool | Nature view

5.0
Outstanding(202 ratings)
Port Republic, Solomons Island, Maryland, United States
View deal
House Shady Side
from $741 per night
House ∙ 13 guests ∙ 6 bedrooms

Child-friendly lovely house with terrace, BBQ & garden | Suitable for remote work | Pet-friendly

5.0
Outstanding(20 ratings)
Shady Side, Anne Arundel County, Maryland, United States
View deal
House Reedville
from $355 per night
House ∙ 9 guests ∙ 4 bedrooms

Child-friendly nice vacation home with patio & BBQ | Perfect for remote work

5.0
Outstanding(27 ratings)
Reedville, Northumberland County, Virginia, United States
View deal
Show all 10075 apartments in Chesapeake Bay

Price and Availability Index in Chesapeake Bay

Click on any bar to see price and availability information

Vacation Rental Price Information in Chesapeake Bay

By constantly analyzing our data, we created a graph to show you the fluctuation of prices in Chesapeake Bay. Booking a vacation rental is most expensive in June. In the period 6/26 – 7/3, you will need to pay $488 on average. On the other hand, the cheapest month in the year is October, with an average vacation rental price of $416.

Rental availability information in Chesapeake Bay

This graph shows how many vacation rentals are available over the next 12 months. Only 10% of the vacation rentals in Chesapeake Bay are available in August. If you'd like to visit then, make sure to book early! You'll find the highest availability in August, with 86% of the vacation rentals in Chesapeake Bay still available.

And we love our apartments

House with terrace, barbecue & garden | Nature view | Good for workation
House with BBQ, terrace & jacuzzi
Fully equipped charming vacation home with patio & barbeque | Beach nearby
Fully equipped vacation home with barbecue & terrace
Family-oriented vacation home with barbeque
Show all 10075 apartments in Chesapeake Bay

Features of Chesapeake Bay vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🏊  Vacation rentals with a pool 4,352 rentals
🌙 Minimum price starting at $83
🐾 Pet friendly vacation homes 3,246 rentals
🏡 Rentals available 9,880 rentals

Beautiful regions abroad to consider for next trip

Beautiful regions near to consider for next trip

image-tag