Vacation rentals in Chesapeake City - HomeToGo base64Hash Vacation rentals in Chesapeake City - HomeToGo

Vacation rentals in Chesapeake City

Browse 24 available vacation homes and compared across 5 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Cabin
    • House
    • Apartment

  • Rating

    • 4.5+
    • 4+

  • Popular amenities

    • Pool
    • WiFi
    • Air conditioning
    • Hot tub
    • Kitchen
    • TV
    • Parking
    • Balcony/patio
    • Fireplace
    • Washing machine
    • Microwave
    • Dishwasher
    • Yard
    • Sauna
    • Crib
    Show more

  • Other Services

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Chesapeake City

Discover your ideal Chesapeake City vacation rental with real-time comparisons of 24 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Chesapeake City
House ∙ 15 guests ∙ 7 bedrooms

House with BBQ, terrace & jacuzzi

Chesapeake City, Cecil County, Maryland, United States
This waterfront house rental in Chesapeake City features a fireplace, kitchen, parking, and direct beach access for 15 guests.
from $744
per night
Outstanding(69 ratings)
from $744
per night
View deal
House Chesapeake City
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped charming house with barbeque, sauna & terrace | Nature view

Chesapeake City, Cecil County, Maryland, United States
This house rental in Chesapeake City features a fireplace, kitchen, and balcony, perfect for a cozy getaway with parking for 4.
from $396
per night
Outstanding(7 ratings)
from $396
per night
View deal
House Chesapeake City
House ∙ 8 guests ∙ 3 bedrooms

House with yard, barbeque & jacuzzi | Nature view

Chesapeake City, Cecil County, Maryland, United States
This waterfront house rental in Chesapeake City features a fireplace, kitchen, balcony, and yard, perfect for family gatherings.
from $222
per night
Outstanding(60 ratings)
from $222
per night
View deal
House Chesapeake City
House ∙ 8 guests ∙ 5 bedrooms

Child-friendly house with yard, hot tub & terrace | Nature view | Pet-friendly

Chesapeake City, Cecil County, Maryland, United States
This Chesapeake City house rental features a pool, hot tub, and a yard, perfect for family gatherings and pet-friendly fun.
from $763
per night
Outstanding(13 ratings)
from $763
per night
View deal
Apartment Chesapeake City
Apartment ∙ 4 guests ∙ 1 bedroom

Children-friendly holiday apartment with yard, terrace & jacuzzi | Nature view | Good for workation

Chesapeake City, Cecil County, Maryland, United States
This waterfront apartment in Chesapeake City features a kitchen, hot tub, yard, and parking for a perfect family getaway.
from $70
per night
Outstanding(14 ratings)
from $70
per night
View deal
House Chesapeake City
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly house with terrace, grill & garden | Dogs allowed

Chesapeake City, Cecil County, Maryland, United States
This waterfront house rental in Chesapeake City features a spacious yard, balcony, and cozy fireplace for a perfect getaway.
from $555
per night
Outstanding(93 ratings)
from $555
per night
View deal
House Chesapeake City
House ∙ 2 guests ∙ 1 bedroom

Vacation home with patio, BBQ & yard | Nature view

Chesapeake City, Cecil County, Maryland, United States
This waterfront house rental in Chesapeake City features a kitchen, fireplace, and yard, perfect for a family getaway for two.
from $98
per night
Outstanding(45 ratings)
from $98
per night
View deal
Cabin Chesapeake City
Cabin ∙ 2 guests ∙ 1 bedroom

Cabin with terrace

Chesapeake City, Cecil County, Maryland, United States
Set in Chesapeake City, this cabin offers a kitchen and family-friendly amenities, perfect for a memorable getaway.
from $124
per night
Excellent(38 ratings)
from $124
per night
View deal
House Chesapeake City
House ∙ 12 guests ∙ 5 bedrooms

House with terrace & barbecue

Chesapeake City, Cecil County, Maryland, United States
This waterfront house rental in Chesapeake City offers a kitchen, balcony, and parking, perfect for gatherings of up to 12.
from $522
per night
Outstanding(48 ratings)
from $522
per night
View deal
House Chesapeake City
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with patio

Chesapeake City, Cecil County, Maryland, United States
This house rental in Chesapeake City offers a kitchen and parking, perfect for a getaway with up to six guests.
from $254
per night
Outstanding(1 rating)
from $254
per night
View deal
House Chesapeake City
House ∙ 7 guests ∙ 2 bedrooms

House with BBQ

Chesapeake City, Cecil County, Maryland, United States
This house rental in Chesapeake City welcomes up to 7 guests and their pets for a memorable getaway by the water.
from $207
per night
Outstanding(1 rating)
from $207
per night
View deal
House Chesapeake City
House ∙ 16 guests ∙ 5 bedrooms

Fully equipped house with patio | City view

Chesapeake City, Cecil County, Maryland, United States
This house rental in Chesapeake City offers a fireplace, kitchen, and parking for up to 16 guests, perfect for group getaways.
from $674
per night
Excellent(14 ratings)
from $674
per night
View deal
Cabin Chesapeake City
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with patio & yard

Chesapeake City, Cecil County, Maryland, United States
This waterfront cabin in Chesapeake City features a kitchen and yard, perfect for a relaxing getaway for four.
from $260
per night
Very good(12 ratings)
from $260
per night
View deal
House Chesapeake City
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly vacation home with terrace, BBQ & jacuzzi | Nature view | Pet-friendly

Chesapeake City, Cecil County, Maryland, United States
This house rental in Chesapeake City features a yard, fireplace, and kitchen, perfect for family gatherings and pets.
from $208
per night
Outstanding(99 ratings)
from $208
per night
View deal
Mobile home Chesapeake City
Mobile home ∙ 6 guests ∙ 1 bedroom

Wonderful mobile home with 1 bedroom for 6 persons

Chesapeake City, Cecil County, Maryland, United States
This RV rental in Chesapeake City offers comfortable sleeping for six and the freedom to explore the scenic surroundings.
from $137
per night
from $137
per night
View deal

Vacation Houses With Pools

Cabin Chesapeake City
from $263
per night
Cabin ∙ 8 guests ∙ 2 bedrooms

Cottage with barbeque, garden & private pool | Good for workation

5.0
Outstanding(24 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pool
View deal
Cabin Chesapeake City
from $255
per night
Cabin ∙ 7 guests ∙ 2 bedrooms

Cottage with terrace & private pool

4.4
Very good(25 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pool
View deal
House Chesapeake City
from $2,054
per night
House ∙ 16 guests ∙ 7 bedrooms

Vacation home with private pool, barbecue & terrace | Nature view | Suitable for remote work

4.9
Outstanding(181 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pool
View deal
See all offers

Dog-Friendly Vacation Rentals

House Chesapeake City
from $362
per night
House ∙ 10 guests ∙ 5 bedrooms

Family-friendly house with garden & barbecue | Nature view | Beach nearby | Pet-friendly

4.9
Outstanding(65 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pet-friendly
View deal
House Chesapeake City
from $811
per night
House ∙ 16 guests ∙ 5 bedrooms

Vacation home with hot tub, garden & grill | Nature view

5.0
Outstanding(53 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pet-friendly
View deal
House Chesapeake City
from $279
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with jacuzzi, patio & yard | Lake view

4.6
Excellent(32 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pet-friendly
View deal
See all offers

Vacation rentals with a balcony

House Chesapeake City
from $299
per night
House ∙ 10 guests ∙ 5 bedrooms

Child-friendly big vacation home with terrace, sauna & barbeque | Nature view

4.9
Outstanding(25 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony
View deal
House Chesapeake City
from $1,083
per night
House ∙ 12 guests ∙ 6 bedrooms

Children-friendly house with sauna, patio & private pool | Nature view | Perfect for remote work | Pets are welcome

5.0
Outstanding(20 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony
View deal
House Chesapeake City
from $337
per night
House ∙ 13 guests ∙ 5 bedrooms

House with patio, garden & BBQ

4.9
Outstanding(177 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Chesapeake City offering exceptional value for money

House Chesapeake City
from $221
per night
House ∙ 7 guests ∙ 3 bedrooms

Children-friendly beautiful house with garden & patio

5.0
Outstanding(28 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
House Chesapeake City
from $147
per night
House ∙ 7 guests ∙ 4 bedrooms

Vacation home | Good for workation

4.9
Outstanding(8 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
Cabin Chesapeake City
from $225
per night
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with BBQ, yard & terrace | Nature view | Suitable for remote work

5.0
Outstanding(160 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal

Top-Rated Vacation rentals in Chesapeake City

Book the highest-rated Chesapeake City vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Chesapeake City
from $360
per night
House ∙ 11 guests ∙ 6 bedrooms

Vacation home with garden, patio & barbecue

4.8
Outstanding(145 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
Cabin Chesapeake City
from $250
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Family-oriented pleasant cottage with terrace, grill & garden | Pets allowed

5.0
Outstanding(53 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
Cabin Chesapeake City
from $158
per night
Cabin ∙ 6 guests ∙ 2 bedrooms

Family-oriented cottage with barbecue & terrace | Nature view

4.9
Outstanding(33 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal

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Trust in the quality and comfort of your stay with verified guest reviews.

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Popular Features & Amenities in Chesapeake City

  • Pool (2)
  • Pet-friendly (3)
  • WiFi (24)
  • Air conditioning (24)
  • Hot tub (4)
  • Kitchen (17)
  • TV (23)
  • Parking (1)
  • Balcony/patio (14)
  • Fireplace (9)
  • Grill (9)
  • Washing machine (14)

Select a filter to search and book a vacation home meeting your requirements among the 24 rentals in Chesapeake City. In Chesapeake City, 2 accommodations include "Pool". Consequently, if you want a rental with a pool, select the Pool filter to compare these accommodations. You can even look for properties if you love sweating the stress away in saunas (1 rentals include "Sauna" in Chesapeake City) or if you need a crib for your baby (2 rentals in Chesapeake City include "Crib").

Spend a delightful Chesapeake City sojourn in a charming vacation home

A historic place steeped in Victorian charm, the scenic Chesapeake City is located on the Chesapeake and Delaware Canal near a spectacular horse country. Taking a trip to this destination makes for an idyllic getaway, especially if you book a beautiful cottage-style vacation home on the waterfront.

Where are the unique attractions in Chesapeake City?

Fun in natural surroundings

Walking on the Chesapeake and Delaware Canal marina is always a pleasurable experience, and the waters are ideal for activities like sailing or fishing. The 1790-acre preserve of Lums Pond State Park, with its picturesque freshwater pond, sports fields, and multi-purpose trails, makes for a recreational destination to spend a fun and relaxed day.

Information about vacation rentals in Chesapeake City

🌙 Nightly prices starting at $79
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 6 homes
🏊 Vacation rentals with pools 3 homes

Frequently Asked Questions

What is the nightly price for a vacation rental in Chesapeake City?

The price of a night's stay in Chesapeake City starts at $79. Nightly prices for house rentals are $641 on average. Bed and breakfast rentals in Chesapeake City cost on average $278 per night.

How many vacation homes are available for booking in Chesapeake City?

There are currently 24 vacation rentals to choose from for your trip.

What are the most popular amenities for vacation rentals in Chesapeake City?

Most travelers search for Pets allowed, Pool, and Internet when booking a vacation rental in Chesapeake City.

How many vacation rentals with pools are in Chesapeake City?

There are 3 vacation homes across 5 providers in Chesapeake City.

Are dogs allowed in vacation homes in Chesapeake City?

In case if you are traveling with a dog in Chesapeake City - 25% of vacation homes allow pets.

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