Chester Rentals By Owner

There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Chester:

• Daniel Boone meets Mid Century Modern Retreatn
• Life on the Farm
• Secluded Family escape w/pool & jacuzzi
• Quarry House Mid-Century Modern
• Equestrian Living: It's a lifestyle "Living on the Farm" Not your ordinary Stay!
• Charming Chester Apartment Steps to Main Street!
• Bimbadeen Loft: Huge Open Plan 2-bedroom! Bring the boat, kids, and the dog!
• Quiet Killingworth Rental with Deck and Grill!
• Mansion on the hill
• New England Colonial home with fabulous Connecticut River views!!

There are many large, family-friendly vacation homes available in Chester; however, here are the most popular family rentals listed on our site:

• Autumn and Winter at the Haddam House
• The Millhouse Downtown Chester
• Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
• COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

Yes, there are 45 self-catering vacation homes in Chester that have hot tubs, swimming pools, & other amenities.

There are more than 45 luxury villas and vacation homes in or near Chester. Filter by price to compare find the most expensive places to stay on Telluridevillas.

Yes, there are 45 pet friendly vacation homes and places to stays that are available in or near Chester that you may consider.