Holiday rentals in Simsbury

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Hidden Cozy Waterfront Eco Cabin Nature Sanctuary

Welcome to Otter Falls Inn! Nestled in the trees directly above the brook and hidden off the main road sits our cozy, vintage eco cottage. Just 8 minutes from all major conveniences, our property is a hidden oasis- an urban nature sanctuary where we are restoring native habitat and the waterway. We lovingly restored and updated the cottage to offer a unique, relaxing, romantic getaway where guests can slow down and enjoy connecting to each other and nature in this stylish, eco conscious home.

River Overlook - Collinsville, CT

Spotless new 1 BR apt (with additional pullout couch in LR)in downtown Collinsville, perched across the street from Farmington River and Rails to Trails. Steps to Collinsville - restaurants, antiques, concerts, walking, biking, fishing, canoe/kayaking. Sleeping for 4 (queen bed in BR, and pullout couch in LR). Relax on your private deck overlooking the river. See if you can spot our local Bald Eagle family! Voted one of "America's 10 Coolest Small Towns" by Frommer's Budget Travel Magazine!

Private Cozy Suite, 0 Fees, Pets Welcome, EV Plug

A private cozy suite for you! Better than a hotel or private room & less than an entire house. Pets welcome with no fees :) Generous discounts for medium- to long-term stays. Your guest suite includes newly furnished living room, apartment kitchenette, large bedroom with full bathroom. Despite many renovations, we kept the vintage & cozy charm. Keurig machine. Separate Wifi for remote work. Less than 20 minutes to the airport and Hartford metro. No cost EV charger on site. No cleaning fees!

Onomea Farm

Relax and watch the sheep graze in the pasture. Enjoy the amazing night sky. Fabulous modern two bedroom handicapped accessible in law suite with separate entrance. Fireplace, washer/dryer, heat, central A/C. Queen bed on main level, King and pull out sofa on 2nd floor. Both bedrooms have 50” TV’s. Full kitchen. Located in North Granby, CT. Quiet location yet close to major attractions and Bradley airport. We have 8 resident well behaved dogs THAT RUN FREE on the property -

The Carriage House Skiing Nearby

Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, SUP, fish and swim. CT Wine Trail and Brignole Vineyards nearby where you'll find food trucks and live music along with award winning wine! Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Mountaintop Horse Farm with Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Loft - Queen Anne Row House in a historic district

Hosted by Judy and Greg, our home is close to art, culture, live theater, and restaurants. Our home is also close to major insurance companies, the state capitol and state of Connecticut offices. You’ll love the cozy 3rd floor loft. We also offer off street parking. Garage space is also available as an option. Our home is a perfect destination for couples, solo adventurers, and business travelers.

Linny’s Lake House - with dock

Linny’s Lake House & Dock Access 🌲🌳 Charming Lakeside Home on South Pond Welcome to our newly renovated lake house tucked into a peaceful 3/4-acre wooded lot, naturally treated to keep mosquitoes and ticks to a minimum. The setting feels calm and restorative, with gentle breezes, shaded trees, and the charm of nearby tobacco fields adding to the sense of being away without being remote.

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!