Holiday houses in West Springfield

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

Location · Family · Layout

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

Location · Hiking · Quiet

Studio ADU Guesthouse near Six Flags

Get ready for thrills and adventure! 🏞️🏰 Our cozy retreat is the perfect base for your Six Flags getaway! 🚗 Located just minutes away from the park, our home offers: Comfortable bedroom with plush bed Fully equipped kitchen for meal prep Relaxing living area for downtime Parking for your convenience Unwind after a day of roller coasters and excitement, and get ready to do it all again the next day! 😎 Book your stay with us and make your adventure unforgettable! 🏠👍

Location · Indoor spaces · Hospitality

3 Bed 2 Bath house in West Springfield.

3 bedrooms/2 baths private house located in West Springfield. 1st floor: Full Kitchen, Dining Room, Living Room, one bath with standing shower, washer&dryer; 2nd floor: 3 Bedrooms(queen size bed each) and one full bath. Parking for up to 4 cars on driveway. Self check in with keypad lock. Close to nearby restaurants, schools, shopping and other more. Easy access to Westfield, Agawam & Springfield Big E - 6min (2.3miles) Baystate - 9min(3.7miles) Six Flags-13min(6.5miles)

Value · Location · Getting around

King Bed w/ Game Room near Massmutual w/ Riverview

Enjoy a stylish, spacious stay in this fully renovated home with nicely decorated bedrooms, two full baths, a full kitchen plus kitchenette, and dining for eight. Have fun in the game room with pool, arcade games, soccer board game, archery, and a huge TV. Relax on the large patio with a beautiful Connecticut River view. Perfect for families and groups seeking comfort, entertainment, and convenience. It’s also near Memorial Dr. and many local attractions and dining.

Location · Family · Walkability

Clean/Spacious 1 bedroom house! (w/parking & yard)

You have the entire space to yourself. Newly painted. Newly refinished hardwood floors throughout. Dining room, Living Room and Kitchen and Front porch, back porch and fenced-in Backyard all for your use. ~Pet fee is $100 for up to 1 pet, $40 for additional pet[per night, they are added guests]~{please add them in your guest count, as I prepare for their stay, as well!} ~ MAXIMUM PETS ALLOWED IS 2 ~ LEVEL 2 EV charger & Tesla adapter AVAIL upon request

Value · Location · Bathroom

Cozy Brick House in Chicopee

Relax with the whole family at this peaceful place to stay. The unit is part of a two family duplex house. You and your family will have the entire unit to yourselves. There are two bedrooms with queen size beds, a living room, kitchen, bathroom, and laundry room. The living room has a TV, fireplace, and Netflix. There is also a fenced in back yard with a patio and outdoor dining area as well as a firepit. The house is also pet-friendly.

Family · Location · Parking

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Value · Location · Kitchen

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!

Location · Family · Air conditioning

Thompson stay or extended stay retreat

Newly remodeled 2nd floor space. Centrally located to major highways, downtown Springfield with the newly opened MGM casino. It's a fantastic spot in the city! Large master bedroom, second bedroom, full kitchen, claw foot bath tub, washer and dryer included. Secure parking. Extended stay is welcomed. No more than 4 people, including children. Additional fee will be charged.

Value · Family · Outdoor spaces

Beautifully Renovated Riverfront Apartment Home

Unwind at this fresh, fully renovated riverfront apartment home with stunning views of the Connecticut River. This home is one of three private apartments located in a 3-family building. The space has been designed with the traveler in mind to be new, clean and very peaceful. This home has absolutely everything you will need for your stay.

Family · Location · View

Linny's | Private Dock | Lake Access | Firepit

✓ Relax, swim, or watch the sunset ✓ Fully equipped renovated kitchen ✓ Self check-in, fast WiFi, free parking ✓ Fire pit and backyard for evenings ✓ Family-friendly and clean throughout ✓ Private dock and lake access on-site

Value · Family · Air conditioning