Holiday rentals in Chestertown - Casamundo base64Hash Holiday rentals in Chestertown - Casamundo

Holiday rentals in Chestertown

Anytime
Guests
Anytime
Guests
23 accommodations available

  • Price per night

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

  • Accommodation types

    • Apartment
    • House
    • Farmhouse

  • Distance to centre

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • Popular amenities

    • WiFi
    • Kitchen
    • Pool
    • Air conditioning
    • TV
    • Washing machine
    • Balcony/patio
    • Parking
    • Microwave
    • Dishwasher
    • Garden
    • Hot tub
    • Fireplace
    • Cot

  • Other Services

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

  • Activities

    • Grill
    • Fishing

Top 15 Recommended holiday lettings in Chestertown

Find your perfect holiday home, apartment or cottage in Chestertown from just £86 per night!

We use AI to generate the short summary in each offer below – check the full description before booking.
House Chestertown
372 m² house ∙ 18 guests ∙ 6 bedrooms

Family-oriented house with private pool, terrace & BBQ | City view | Dogs allowed

Chestertown, Chester, New York, United States
This spacious house rental in Chestertown accommodates up to 18 guests, featuring a private pool, garden, and fireplace, perfect for family gatherings and pet-friendly es...
from £287
per night
Very good(57 ratings)
from £287
per night
Check prices
Lodge Chestertown
186 m² lodge ∙ 8 guests ∙ 3 bedrooms

Family-oriented lodge with garden, terrace & BBQ | Good for workation | Pets are welcome

Chestertown, Chester, New York, United States
Experience the perfect family getaway in this spacious lodge in Chestertown, featuring a garden, hot tub, and fireplace. With room for eight and pet-friendly amenities, i...
from £171
per night
Outstanding(57 ratings)
from £171
per night
Check prices
House Chestertown
87 m² house ∙ 8 guests ∙ 1 bedroom

Children-friendly house with terrace, barbecue & hot tub | Mountain view | Suitable for remote work

Chestertown, Chester, New York, United States
This spacious house in Warrensburg offers stunning mountain and lake views, a fireplace, hot tub, and a family-friendly kitchen. Perfect for up to 8 guests, with ample pa...
from £186
per night
Outstanding(29 ratings)
from £186
per night
Check prices
House Chestertown
House ∙ 9 guests ∙ 3 bedrooms

Holiday home with barbecue, garden & terrace

Chestertown, Chester, New York, United States
This spacious house rental in Warrensburg welcomes pets and features a fireplace, fully equipped kitchen, garden, and parking for up to nine guests, making it perfect for...
from £187
per night
Outstanding(6 ratings)
from £187
per night
Check prices
House Chestertown
93 m² house ∙ 6 guests ∙ 3 bedrooms

Holiday home with pool, barbeque & garden | Lake view

Chestertown, Chester, New York, United States
This delightful house rental in Chestertown accommodates six guests and features a private pool, hot tub, stunning lake and mountain views, and a lovely garden, perfect f...
from £334
per night
Outstanding(14 ratings)
from £334
per night
Check prices
House Chestertown
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, jacuzzi & BBQ

Chestertown, Chester, New York, United States
This delightful house rental in Chestertown accommodates up to six guests and features a welcoming fireplace, a family-friendly kitchen, a lovely garden, a relaxing hot t...
from £171
per night
Outstanding(18 ratings)
from £171
per night
Check prices
House Chestertown
200 m² house ∙ 11 guests ∙ 4 bedrooms

Children-friendly holiday home with terrace & barbeque

Chestertown, Chester, New York, United States
This stunning house rental in Chestertown accommodates up to 11 guests and features a welcoming fireplace, a fully equipped kitchen, family-friendly amenities, and conven...
from £219
per night
Outstanding(4 ratings)
from £219
per night
Check prices
House Chestertown
120 m² house ∙ 8 guests ∙ 3 bedrooms

House with garden | Mountain view | Suitable for remote work

Chestertown, Chester, New York, United States
This fantastic house rental in Horicon accommodates up to 8 guests and features a cosy fireplace, a spacious kitchen, a beautiful garden, and stunning mountain views, per...
from £178
per night
Outstanding(25 ratings)
from £178
per night
Check prices
Cabin Chestertown
54 m² cabin ∙ 4 guests ∙ 2 bedrooms

Cabin with pool, garden & terrace | Lake view

Chestertown, Chester, New York, United States
A delightful cabin in Chestertown, perfect for families, offering stunning lake and mountain views, a inviting fireplace, a well-equipped kitchen, and a lovely garden by ...
from £214
per night
Outstanding(32 ratings)
from £214
per night
Check prices
House Chestertown
98 m² house ∙ 6 guests ∙ 3 bedrooms

Holiday home with pool, barbecue & garden | Lake view

Chestertown, Chester, New York, United States
This delightful house rental in Chestertown accommodates up to 6 guests and features a pool, fireplace, kitchen, and family-friendly garden with stunning lake and mountai...
from £321
per night
Outstanding(22 ratings)
from £321
per night
Check prices
Cottage Chestertown
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with BBQ & terrace | Lake view

Chestertown, Chester, New York, United States
This delightful cottage in Chestertown accommodates four guests, featuring stunning lake views, a welcoming fireplace, a fully equipped kitchen, and pet-friendly options....
from £193
per night
Outstanding(63 ratings)
from £193
per night
Check prices
House Chestertown
House ∙ 10 guests ∙ 4 bedrooms

Lovely holiday home with terrace & garden | Mountain view

Chestertown, Chester, New York, United States
This stunning house rental in Chestertown accommodates up to 10 guests, featuring a well-equipped kitchen, a beautiful garden, and breathtaking lake and mountain views, p...
from £450
per night
from £450
per night
Check prices
Cabin Chestertown
65 m² cabin ∙ 4 guests ∙ 2 bedrooms

Family-oriented pleasant cabin with barbecue, pool & garden | Lake view

Chestertown, Chester, New York, United States
This delightful cabin in Chestertown accommodates up to 4 guests and features stunning lake and mountain views, a pool, a fireplace, and a family-friendly garden. Book no...
from £243
per night
Very good(16 ratings)
from £243
per night
Check prices
House Chestertown
84 m² house ∙ 8 guests ∙ 4 bedrooms

Holiday home with pool, garden & BBQ | Mountain view

Chestertown, Chester, New York, United States
This stunning house rental in Chestertown accommodates up to 8 guests, featuring a pool, fireplace, kitchen, and beautiful lake and mountain views, all in a family-friend...
from £237
per night
Outstanding(23 ratings)
from £237
per night
Check prices
House Chestertown
279 m² house ∙ 10 guests ∙ 4 bedrooms

House with 4 bedrooms for 10 persons

Chestertown, Chester, New York, United States
Experience the perfect getaway in Horicon with this spacious house rental, accommodating up to 10 guests. Enjoy modern amenities and a welcoming atmosphere for unforgetta...
from £339
per night
Outstanding(3 ratings)
from £339
per night
Check prices

Best holiday rentals with a balcony

Scenic views await in Chestertown - book a holiday rental with a private balcony!

We use AI to generate the short summary in each offer below – check the full description before booking.
House Chestertown
from £371 per night
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented house with terrace & BBQ | Lake view | Perfect for remote work

5.0
Outstanding(14 ratings)
Chestertown, Chester, New York, United States
Balcony
Check prices
House Chestertown
from £154 per night
112 m² House ∙ 6 guests ∙ 3 bedrooms

Family-oriented holiday home with barbeque & terrace | Lake view | Good for workation | Pets are welcome

5.0
Outstanding(5 ratings)
Chestertown, Chester, New York, United States
Balcony
Check prices
House Chestertown
from £328 per night
160 m² House ∙ 8 guests ∙ 3 bedrooms

Fully equipped ample house with sauna & barbeque

5.0
Outstanding(10 ratings)
Chestertown, Chester, New York, United States
Balcony
Check prices
See all offers

Holiday homes with a patio or terrace

Sunset serenity: Book your Chestertown holiday rental with a private terrace - relaxation awaits!

We use AI to generate the short summary in each offer below – check the full description before booking.
House Chestertown
from £184 per night
186 m² House ∙ 8 guests ∙ 3 bedrooms

House with garden, terrace & jacuzzi | Mountain view | Good for workation

4.9
Outstanding(46 ratings)
Chestertown, Chester, New York, United States
Balcony/Patio
Check prices
House Chestertown
from £275 per night
195 m² House ∙ 8 guests ∙ 3 bedrooms

Child-friendly house with terrace, garden & barbeque | Lake view | Dogs allowed

4.9
Outstanding(57 ratings)
Chestertown, Chester, New York, United States
Balcony/Patio
Check prices
House Chestertown
from £545 per night
House ∙ 17 guests ∙ 5 bedrooms

Holiday home with barbeque, terrace & hot tub | Lake view

5.0
Outstanding(2 ratings)
Chestertown, Chester, New York, United States
Balcony/Patio
Check prices
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Frequently asked questions

What are the most popular accommodations in Chestertown?

The most popular accommodation types in Chestertown are house rentals and cabin. With 23 accommodations in Chestertown, the perfect holiday home is only one click away.

What does it cost to rent a holiday home in Chestertown?

With Casamundo you can find rentals in Chestertown starting at £86. On average, you will stay in a 62 m² (Cabin) or a 143 m² (House rentals).

Do you also offer accommodations that are suitable for groups in Chestertown ?

We have a great range of accommodations for groups in Chestertown. On average, the house rentals has space for 8 guests.

Top cities to visit

Most popular holiday destinations around Chestertown

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