Holiday rentals near Playhouse on Park

We found 410 holiday rentals — enter your dates for availability

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August 2025

September 2025

If you'd like to stay close to Playhouse on Park, scroll through and discover private holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the amenities that you expect and more, which might include air conditioning and a pool. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Playhouse on Park

Showing deals for:21 Nov - 28 Nov

Exceptional

(25 reviews)

Family Friendly Lake House: Lake Pocotopaug, Fire-pit, Kayaks, Canoe. Sunsets.

East Hampton, CT

8% off

S$692 nightly

Includes taxes & fees

Exceptional

(120 reviews)

Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

Middle Haddam, CT

8% off

S$889 nightly

Includes taxes & fees

Exceptional

(15 reviews)

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Broad Brook, CT

8% off

S$178 nightly

Includes taxes & fees

Wonderful

(7 reviews)

A “Wow” Experience everywhere there is something to stimulate your mind Interest

Windsor, CT

8% off

S$465 nightly

Includes taxes & fees

Exceptional

(7 reviews)

NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly

Rocky Hill, CT

8% off

S$493 nightly

Includes taxes & fees

Gorgeous log cabin with exposed log trusswork and original pine floors

Exceptional

(22 reviews)

Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home

Harwinton, CT

7% off

S$351 nightly

Includes taxes & fees

Exceptional

(10 reviews)

Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!

Avon, CT

8% off

S$431 nightly

Includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Playhouse on Park

Beautiful Sunset view from the Lakefront decks

Spectacular Lakefront home with expansive decks

Sleeps 8 · 4 bedrooms · 2 bathrooms

Your Dream Vacation Stars Here!
Feel Nature, Live Luxury. By the Lake

Lakefront Luxury House, with Kayaks, Fire pit, Game Room and Home Theater!

Sleeps 15 · 5 bedrooms · 5+ bathrooms

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Sleeps 6 · 2 bedrooms · 1+ bathroom

Top rated rentals - Playhouse on Park

Incredible stay

We had one the best ever experiences staying at this house. Carl and Rafa have gone out of their way to create a magical abode that goes well beyond expectations. Their attention to detail is unsurpassed and as a result makes for an incredible stay. They have thought of every little detail for their guests to be incredibly comfortable throughout the stay. We had the opportunity to stay both in the suite on the first floor as well as the entire lower level during our stay and they both were superb. The landscaping, outdoor space and spectacular bird life make this home a must visit. We will be booking it again next year.

Kim D.

Stayed Jul 2023

Phenomenal

We had the most perfect stay ever at this magical abode. Carl and Rafa are incredibly gracious hosts who have gone well out of their way to ensure their guests have the most memorable stay. We will be back!

Kim D.

Stayed Jul 2023

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value