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

Holiday rentals in Chestertown

Anytime
Guests
Anytime
Guests
25 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+

  • Services

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

  • Accommodation type

    • 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 £149 per night!

House Chestertown
130 m² house ∙ 8 guests ∙ 4 bedrooms

Fully equipped big house with BBQ, terrace & garden | Lake view

Chestertown, Chester, New York, United States
This delightful house rental in Chestertown accommodates up to 8 guests, offering a stunning lakeview, a charming garden, a cozy fireplace, and convenient parking just st...
from £249
per night
Outstanding(54 ratings)
from £249
per night
Check prices
House Chestertown
264 m² house ∙ 8 guests ∙ 6 bedrooms

Child-friendly holiday home with garden, terrace & jacuzzi | Mountain view

Chestertown, Chester, New York, United States
This spacious house rental in Brant Lake offers stunning mountain views, a hot tub, and a family-friendly garden, perfect for gatherings of up to 10 people. Enjoy cozy ev...
from £411
per night
Excellent(42 ratings)
from £411
per night
Check prices
House Chestertown
188 m² house ∙ 6 guests ∙ 4 bedrooms

Child-friendly ample house with garden | Nature view

Chestertown, Chester, New York, United States
A delightful house rental in Chestertown, perfect for families, featuring a garden, fireplace, and fully equipped kitchen. With parking available, this spacious retreat a...
from £195
per night
Very good(45 ratings)
from £195
per night
Check prices
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 £297
per night
Very good(57 ratings)
from £297
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 £204
per night
Outstanding(28 ratings)
from £204
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 £190
per night
Outstanding(57 ratings)
from £190
per night
Check prices
House Chestertown
House ∙ 6 guests ∙ 3 bedrooms

House with garden, jacuzzi & barbeque | Mountain view | Suitable for remote work

Chestertown, Chester, New York, United States
This delightful house rental in Chestertown offers stunning lake and mountain views, a relaxing hot tub, family-friendly amenities, a fireplace, and a spacious garden—per...
from £88
per night
Outstanding(39 ratings)
from £88
per night
Check prices
House Chestertown
121 m² house ∙ 10 guests ∙ 3 bedrooms

Holiday home with garden, BBQ & terrace | Nature view

Chestertown, Chester, New York, United States
A beautiful Brant Lake house rental, perfect for families and pets, accommodating up to 10 guests. Enjoy the garden, waterside views, a fireplace, and a spacious balcony ...
from £207
per night
Excellent(31 ratings)
from £207
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 £214
per night
Outstanding(6 ratings)
from £214
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 £167
per night
Outstanding(17 ratings)
from £167
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 £181
per night
Outstanding(63 ratings)
from £181
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 £303
per night
Outstanding(22 ratings)
from £303
per night
Check prices
House Chestertown
138 m² house ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with terrace & barbecue | Nature view

Chestertown, Chester, New York, United States
This delightful house rental in Chestertown offers a warm fireplace, well-equipped kitchen, inviting balcony, and convenient parking, perfect for a memorable getaway for ...
from £240
per night
Very good(1 rating)
from £240
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 £232
per night
Outstanding(23 ratings)
from £232
per night
Check prices
Farmhouse Chestertown
195 m² farmhouse ∙ 7 guests ∙ 3 bedrooms

Fully equipped farm with barbeque, garden & terrace

Chestertown, Chester, New York, United States
This delightful farmhouse rental in Chestertown accommodates up to 7 guests and features a spacious kitchen, a charming garden, and ample parking. Ideal for a memorable g...
from £190
per night
Very good(5 ratings)
from £190
per night
Check prices

Pet-Friendly Holiday Homes

Reserve a pet-friendly holiday rental in Chestertown - plan your paw-fect getaway!

House Chestertown
from £548 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
Pet-friendly
Check prices
House Chestertown
from £273 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
Pet-friendly
Check prices
House Chestertown
from £149 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(4 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Check prices
Show more offers

Best holiday rentals with a balcony

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

House Chestertown
from £440 per night
146 m² House ∙ 10 guests ∙ 5 bedrooms

Holiday home with terrace, garden & barbeque | Lake view

4.7
Excellent(69 ratings)
Chestertown, Chester, New York, United States
Balcony
Check prices
House Chestertown
from £268 per night
125 m² House ∙ 6 guests ∙ 3 bedrooms

Children-friendly spacious house with garden, BBQ & terrace

4.9
Outstanding(84 ratings)
Chestertown, Chester, New York, United States
Balcony
Check prices
House Chestertown
from £360 per night
300 m² House ∙ 22 guests ∙ 7 bedrooms

House with BBQ, garden & terrace | Lake view | Perfect for remote work

5.0
Outstanding(128 ratings)
Chestertown, Chester, New York, United States
Balcony
Check prices
See all offers

Frequently asked questions

What are the most popular accommodations in Chestertown?

The most popular accommodation types in Chestertown are house rentals and cabin. With 25 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 £149. On average, you will stay in a 62 m² (Cabin) or a 152 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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