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:

• Quarry House Mid-Century Modern
• Equestrian Living: It's a lifestyle "Living on the Farm" Not your ordinary Stay!
• 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!!
• Tuscan Villa in Chester CT
• Carriage House Studio Apartment
• Cozy Apartment in Antique Home on Second Floor in East Haddam, CT
• Connecticut Colonial with River and Sunset Views!

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

• COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
• The Millhouse Downtown Chester
• Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
• Resort style getaway w/pool, spa, game room & more

Yes, there are 44 self-catering vacation homes in Chester that have hot tubs, swimming pools, & other amenities.

There are more than 44 luxury villas and vacation homes in or near Chester. Filter by price to compare find the most expensive places to stay on Maimonbeach.

Yes, there are 44 pet friendly vacation homes and places to stays that are available in or near Chester that you may consider.