Title: The Best 5 Star Hotels in Greenfield, MA from $258 | Expedia.com

[Greenfield Travel Guide](https://expedia.com/Greenfield.dx8027)[Hotels in Greenfield](https://expedia.com/Greenfield-Hotels.d8027.Travel-Guide-Hotels)[Vacation Rentals in Greenfield](https://expedia.com/Greenfield-Vacation-Rentals.d8027.Travel-Guide-VacationRentals)[Flights to Greenfield](https://expedia.com/Cheap-Flights-To-Greenfield.d8027.Travel-Guide-Flights)[Car Rentals in Greenfield](https://expedia.com/Car-Rentals-In-Greenfield.d8027.Car-Rental-Guide)[Greenfield Vacation Packages](https://expedia.com/Greenfield.d8027.Destination-Travel-Guides)

![The Mohawk Trail through The Berkshire Hills (Massachusetts, USA) in autumn](https://images.trvl-media.com/place/8027/451ceee3-7430-40be-a0f3-4fdb2dca05a5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Greenfield 5 Star Hotels

Tonight

[Apr 8 - Apr 9](https://www.expedia.com/Hotel-Search?regionId=8027&startDate=2026-04-08&endDate=2026-04-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Apr 9 - Apr 10](https://www.expedia.com/Hotel-Search?regionId=8027&startDate=2026-04-09&endDate=2026-04-10&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=8027&startDate=2026-04-10&endDate=2026-04-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

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## Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Greenfield.

![Chesterfield Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/7179648d_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Chesterfield Inn

20 Cross Roadd West West Chesterfield NH

$301 nightly

$327 total

Apr 19 - Apr 20

Total with taxes and fees

[](https://expedia.com/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information)

![Inn on Putney Road](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Inn on Putney Road

192 Putney Road Brattleboro VT

$235 nightly

$258 total

Apr 9 - Apr 10

Total with taxes and fees

9.8/10 Exceptional! (57 reviews)

[](https://expedia.com/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information)

![The Brattleboro](https://images.trvl-media.com/lodging/84000000/83090000/83087000/83086930/e1d2b1c7_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Brattleboro

770 South St Brattleboro VT

[Get rates](https://expedia.com/Hotel-Search?startDate=4%2F22%2F2026&endDate=4%2F23%2F2026&selected=83086930&PinnedHotelID=83086930&HadPinnedHotel=true&regionId=8027)

10/10 Exceptional! (5 reviews)

[](https://expedia.com/Brattleboro-Hotels-The-Brattleboro.h83086930.Hotel-Information)

Still don't see what you're looking for?

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[Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&regionId=8027&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&regionId=8027&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&regionId=8027&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&regionId=8027&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&regionId=8027&star=50&star=50&amenities=WATER_PARK)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

## Learn more about Greenfield

Stroll down Main Street to discover charming local shops and the historic Garden Theater, where live performances still enchant audiences. Nearby, outdoor enthusiasts can hike the Poet's Seat Tower trail for panoramic views or paddle along the serene Deerfield River in neighboring Deerfield.

[See all hotels in Greenfield](https://www.expedia.com/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&adults=2&regionId=8027)

![The Mohawk Trail through The Berkshire Hills (Massachusetts, USA) in autumn](https://images.trvl-media.com/place/8027/451ceee3-7430-40be-a0f3-4fdb2dca05a5.jpg?impolicy=fcrop&w=900&h=563&p=1&q=high)

## Top Greenfield Hotel Reviews

## Find out more about Greenfield

Why not ask for complete opulence during your jaunt to Greenfield? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Greenfield so popular in the last year. There's no reason to delay a getaway to Greenfield any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Book one of Expedia's luxurious 5-star hotels in Greenfield and get ready to be pampered like never before. What are you waiting for?

### Book the Best Greenfield 5-Star Hotels

A stay in one of these hotels is bound to be wonderful. Exceptional customer care, luxurious bedding, and fabulous spa offerings are all on offer. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. What creature comforts do you want in your lodging? A concierge to help you suggest the next attraction to visit? A full-body massage to help your cares fall away? Plush carpeting, piping hot coffees, and even space for your family pet in some cases...these hotels will astonish you. 

You won't sleep and order room service the entire time, though. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Greenfield are the perfect place to relax after a busy day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs. 

### Your Getaway Starts Today

The results are in, and Greenfield 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Choose one of the 5-star hotels in Greenfield today and soothe yourself in the lap of luxury tomorrow.

## Frequently asked questions

### How much does it cost to stay in a 5-star hotel in Greenfield?

> - Search for the lowest price per night from $258

### What makes a hotel 5 stars in Greenfield?

### Are there any 5-star all-inclusive resorts in Greenfield?

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