Holiday rentals in Wallingford

Honey, I’m home. New England Charmer

15 mins from historic New Haven and Yale you'll find a family friendly escape in this charming colonial just steps from a quaint classic New England Main St. 1/2 mile walk to Choate. 5 min drive to Quinnipiac U, N Haven Campus. 1 min walk to the Wallingford YMCA and Doolittle Park with lit tennis courts, basketball, baseball and playground. Don't miss the Garden Market on Saturdays! Or stay home and watch the birds from the kitchen window seat. We want to welcome you to your home away from home.

Newly Restored Cottage on River

Newly restored cottage, after being off Airbnb for 5 years, with cathedral living/kitchen area. Indoor/outdoor fireplaces & views of the stone sculpted grounds on the West River. The bedroom is on the ground floor with bath & wood stove. There are miles of trails across the river at Bittner Park. Bittner has a beautiful 18 hole disc golf course, pickle ball courts, basketball and a running track. A 1/4 mile away by car or a 5 minutes walk over the "Peter Pan Bridges"-not for the faint of heart.

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

Private Bright Studio Retreat with kitchen

Forget your worries in this spacious and serene space. This inviting space offers a haven of natural light, providing a warm and welcoming atmosphere throughout the day. Whether you're seeking a cozy hideaway, an inspiring workspace, or a versatile entertainment area, this basement retreat offers endless possibilities to suit your lifestyle. With its thoughtfully planned layout and attention to detail, you'll find comfort and serenity beneath the surface in this unique and inviting space.

The Garden Loft - A Charming New England Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

Wallingford Getaway

ENJOY DAILY CONTINENTAL BREAKFAST INCLUDED WITH minimum two night stay. Experience a cozy stay in our spacious 1300 square foot unit with included breakfast. Choose from muffins, bagels, bars and yogurt. Enjoy a relaxing afternoon with a cup of Java from your own Keurig. This unit features a comfy red electric red reclining couches and a flat screen TV. The kitchen area is equipped with a toaster microwave convection oven and fridge.

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

Guilford Field House

Enjoy a wonderful guest house with all the amenities on a historic property in Guilford, Connecticut. The main house built in 1779 extends its character to the guest house which has views of an open field. On property there is a working restored horse barn. We are minutes to the spectacular downtown area of Guilford and easy access to Durham, Madison, and other surrounding towns and highways!

Spacious in-law apartment steps from Choate

Private apartment with private entrance. This cute apartment is located in the center of town, close to Choate Rosemary Hall and downtown Wallingford. Very safe and charming neighborhood. Off street parking included. The private space includes a combination living, dining room, and full kitchen. Private bathroom with clean shower and amenities. Beautiful backyard with a pretty patio

Haven House - 12 min to Yale!

Amazing home away from home. Minutes away from New Haven, Yale University and Quinnipiac University. 2 very spacious bedrooms with queen beds. A dedicated family room for work or relaxing. Beautiful new kitchen with bar stool counter and separate dining room! Outdoor patio and a huge, peaceful back yard completes this amazing package of a home! Parking is free in the driveway.