1. The Round House

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Colrain, MA

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The Round House

2.9 (15 reviews)

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One of the cubby-style beds at the Roundhouse
April K.

We had our October wedding at the roundhouse with 56 guests. The October foliage and scenic views were amazing this time of year. We chose the roundhouse because it accommodated our friends and family that wanted to stay over night, there was a separate house for the bride and groom and the owner included brunches and dinner cooked onsite at a reasonable price. Pro's - Rebecca's food was amazing. The brunches and dinners were incredible, some of the best food I ever had. The venue is eclectic, this is my style, it might not be yours. Con's - a few of the guests left early because the beds were uncomfortable or didn't meet their needs - also be aware that this is a DIY venue, so there may be a lot of ground work if your having a wedding here. Please note, this is not a holiday inn, if you require privacy or a posture-pedic pillow top mattress, than this is not for you. However, if your open-minded and want a unique experience full of story telling, great food, instruments, hats and books everywhere and a nice bon-fire outside at night...then this is your place! We hoped for an outdoor ceremony, but it ended up raining. Inside the roundhouse we accommodated 54 people for dinner...it was tight, but we made it happen. I would not recommend more people than that. If you can plan on an outside wedding with a tent then you could have more. We did the entire wedding ourselves, we bought all the wine and alcohol and had a self serve bar and kegs. We rented all the dishes, glasses, tables, table clothes etc... We put everything up, we took everything down. It was a lot of work. So my recommendation is to understand what your getting into or else hire someone else to do it! In the end, I wouldn't change a thing. We have amazing memories and photos of an amazing place. We got to share an entire weekend with friends and family and had a wedding too. Just a note on the dogs - they were well hidden during the wedding and never a problem. On the days they were out, they were well mannered. As some of the earlier recommendations implied, the owner of the roundhouse is a strong personality, but we were able to work with her. She did have a few "rules of the roundhouse" that everyone followed, a few guests rolled their eyes as she explained with painstaking clarity how to hold on to your coffee cup and napkin for two days so she didn't have to clean them twice. We had to make our beds after our visit and deposit our linens to a central location, anything that was moved out of place had to be put back in place. We had very specific instructions from time to time, but overall Rebecca made it happen and her food was really, really amazing!

Musical instruments everywhere, experimentation is encouraged!

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Lily's Lodge

Lily's Lodge

5.0(2 reviews)
38.7 mi

Just stayed the night here on a road trip. Owners are very kind. The inside was clean and comfy…read more Tons of room. Muffins were waiting for us which was lovely. The next day we had an amazing breakfast at the restaurant across the street. Would stay there again. Only downside is the outside doesn't match how nice the inside is.

Lily's Lodge was fabulous! A+++! We had 3 adults and 3 youths in our party. We were there to…read morecelebrate my son's 11th birthday with a weekend getaway to Six Flags Fright Fest. All the rooms are extra spacious. There is actually enough bedding for 9 people. We had a whole house to ourselves! Plenty of parking! All rooms, including bedding, sofas and bathrooms were super clean. The home smelled great when we walked in and there were fresh muffins waiting for us. The contemporary deco was fun while still providing a home away from home feel. The owners have a restaurant named Memo's across the street. We had a fabulous breakfast at Memo's at very reasonable prices. I had mentioned to the owner Christine that it had been my son's birthday the night while we were checking in. The next morning while we had breakfast at Memo's without being asked the owner and restaurant staff surprised my son with a chocolate muffin and candle and a birthday song. It was nice of her to remember and It made the start of his birthday getaway weekend very special. Christine was super attentive to our needs and answered any questions we had as 1st timers there. Lily's Lodge was just 10 minutes from 6 Flags and is right across the street from the annual Big E entrance. While staying at Lily's Lodge it felt like were were truly away yet still had very easy access to the main road which makes it convenient for quick trips to grab last minute items you may have forgotten to pack or just to do some shopping. We look forward to being future guests at Lily's Lodge again. It was a delightful find! Thanks Christine for your hospitality!

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Lily's Lodge - Newly renovated lodge

Newly renovated lodge

Lily's Lodge - Across the street from the Eastern States Exposition and less than 5 minute drive to downtown Springfield Ma

Across the street from the Eastern States Exposition and less than 5 minute drive to downtown Springfield Ma

Lily's Lodge

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1868 Crosby House - Escape to our secret gardens!

1868 Crosby House

4.9(15 reviews)
14.4 mi

I have almost forgotten how wonderful it can be to stay in a great B&B, and this one certainly…read morerestored my passion for it -- and then some. From the street it looked like a charming New England B&B and there are plenty of those in the area. What sets this particular one apart, in my opinion, are the following: * At the back of this charming home is a beautifully crafted, lush garden with a hammock and benches placed in strategic nooks designed for optimal book-reading or daydreaming. At the top of the small hill is a pergola -- for more daydreaming, or if you are a bride-to-be looking for a romantic venue, this tops the cake. * The added bonus: you get your own entrance to a walking trail (please see picture below) that connects to a network of trails. It's beautiful now in the the summer time. I imagined how much more beautiful it will be in autumn. I must come back. * The breakfasts are to die for!! Imaginative and definitely gourmet. BTW, I had stayed in some expensive hotels before (the Four Seasons, etc.) -- in my opinion, this B&B's breakfast is better. Way, way better. On my first day, the second course was freshly-baked frittata with a side of steamed kale and zucchini -- picked from their garden. The cheese had just the right gooey to it, and the eggs were fluffy. Day 2: French-toasted croissant filled with creamy custard and drizzled with maple-orange syrup. Yum! * The Owner, Lynn is a wonderful person who had lived in Brattleboro for a very long time and knows its ins and outs -- from where to get great cheese to Brattleboro's unique home architectures. Engaging when a guest needed help and wonderfully welcoming. Yet, I always felt I had my privacy. She has mastered how to be a great host. BTW, the rooms are clean and well kept with a touch of history and modern amenities -- for example: I had a double shower head (a rain shower and a handheld). One last thing: In a hotel or an Airbnb, I always felt unsafe -- locked and double locked. In contrast, in the three days that I stayed here, I left my windows open at night to feel the cool evening breezes from the garden, and during the day, I left my door unlocked while I ate breakfast at the dining room. Priceless. I would come back for the breakfast, or the garden and walking trails, or the wonderfully warm, welcoming atmosphere -- better still, get all three. This one is definitely worth going back to again and again whenever I find myself looking for a great place to stay in Vermont. Highly recommended!

"LIKE FAMILY!"…read more Richard and Lynn treat you like you family from start to finish!!!! We were in awe of the home, the decor, the homemade desserts, the little touches that made our trip very special. The suite was extremely clean and stocked with lovely linens, fresh fruit, coffee, and even fresh autumn leaves for a beautiful decorative flair. They were kind enough to pick us up from the Amtrak station and really attended to our every need. The suite was more than we had imagined, and the online pictures really do not do the Crosby House justice! Thanks The Crosby house for making our stay relaxing, romantic, and unbelievable!!!

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1868 Crosby House - The cozy Autumn Rose room

The cozy Autumn Rose room

1868 Crosby House - Beautiful Brattleboro!

Beautiful Brattleboro!

1868 Crosby House

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The Lake House Guest Cottages of the Berkshires - Sunset Cheers

The Lake House Guest Cottages of the Berkshires

5.0(3 reviews)
31.5 mi

Our daughter had her wedding here this past weekend and it could not have been a better experience!…read more Nicole, who runs the Lake House is a cornerstone of why this place is so special and works so well. Nicole is not only incredibly organized and thorough but she gives tremendous advise too. The cottages are lovely and spotless due to her focus on the details and big picture. With Nicole as manager, we are considering renting some of the cottages for an extended family winter vacation. Nicole and everyone on her team are courteous and helpful, setting a wonderful tone. The neighborhood is just ok but once you walk onto the property, you'll see why its a little oasis, right on the lake. The cottages are lovely --modern with full nice kitchens, fireplaces, comfortable beds, etc. We used local vendors which worked out so well! They all had worked on the property and with each other so it was flawless. We had such a good experience, we're considering renting some of the cottages for a family reunion. Thank you to Nicole and her team for helping create such a magical experience!

Gorgeous luxury lake house cottages. We stayed at the Artist cottage. 2 double bed n 1 pull out…read morecouch. So technically can sleep 6. Cory the groundskeeper Keri's the place pristine. Anything you need he can accommodate. He brought the grill in front of our house so we can have bbq. I love the lake access n all the things you need for water sport. Kayak, paddle buses, canoe, paddle boat. Amazing. After all you daily activities a sit in front n watch the sunset. We also rented a pontoon boat to explore the lake. It was an snacking vacation

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The Lake House Guest Cottages of the Berkshires - Smores

Smores

The Lake House Guest Cottages of the Berkshires - Paddle board

Paddle board

The Lake House Guest Cottages of the Berkshires - Sunset

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Sunset

Chesterfield Inn

Chesterfield Inn

4.7(55 reviews)
18.2 mi
•$$$

Relaxing restaurant setting. Tables are nicely spaced so you can have a table discussion without…read morebothering tables around you. Staff is very pleasant. Always looking after you without overdoing it. Menu is seasonal particularly the produce. The protein offerings only change about twice a year. My wife had the rack of lamb and I had the duck. Both were very good. We have been there several times and have never felt rushed at all. Judy and her team do a great job.

Always love our stays - and leave looking forward to our next trip!!!!…read more Staying at the Chesterfield Inn Bed and Breakfast is never a disappointment. From the moment you walk in you are treated with warm hospitality by the owners Judy & Phil along with their staff. Something that stands out is the staff have been the same, which speaks for the owners. I can't say enough about how friendly, accommodating, and welcoming, everyone. We stayed in the main building, in rooms 17, 15, 12 & 14 all have cozy accommodations that are spacious and very clean. Room 15 was a two-room suite with a gas fireplace that we enjoyed in the evening. Room 14 also has a gas fireplaced that we enjoyed. Our favorite room is 12 on the first floor with a private balcony. All the rooms have very comfortable beds, and each room has a small refrigerator. Each of these rooms all had a view of the mountains in the background. Breakfast is included and is served in the lovely dining room. Thersa is very friendly and always ensures we have everything. Breakfast starts with fresh baked muffins and fruit. There is always a selection for breakfast from eggs, omelets and either French toast, waffles or pancakes. I have enjoyed different omelets, the Cinnamon French toast, waffles w/strawberries and blueberry pancakes served with warm maple syrup that comes from a local farm. In the afternoon you can relax by the fireplace in the parlor and enjoy a cup of coffee or tea with a variety of fresh baked cookies that are set up for your enjoyment. I highly recommend having dinner in the dining room that is right on the premises at least one night during your stay. The chef prepares great meals, and the menu has a very nice selection. Service has always been exceptional. There is a nice selection of wine, beer and specialty cocktails to choose from. I would highly recommend taking a ride to the "Vermont Country Store" during your stay. The store brought us back to our childhood with the nostalgic toys, rows of penny candy and the original tins of "Charlie chips and much more! Judy and Phil, along with all their staff, are very kind and caring. Thank you all very much for a lovely stay. See you on our next stay. Kathy & Ray Milford, CT

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Chesterfield Inn
Chesterfield Inn
Chesterfield Inn

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Howarth House Bed and Breakfast - Howarth House B&B

Howarth House Bed and Breakfast

5.0(17 reviews)
44.2 mi

This place is wonderful! I have now stayed there with my husband and son twice and we were blown…read moreaway. The rooms are lovely and clean and the massive bathroom has a luxurious shower . The breakfast is outstanding: there is a cooked-to-order menu (with eggs from their own chickens!) and a beautiful set-up in a sun room overlooking the nature reserve in the backyard. The property has a beautiful pool and my son loved the game room with a pool table. The very friendly owners, also the chefs, clearly pay attention to detail!

A wooded oasis one minute from Fitchburg State, 1.5h by train from Boston!…read more Visiting family in Fitchburg, we wanted to stay close to the center of town, and we were so lucky to find availability at Howarth House B&B! This beautiful wooded oasis is just up the hill from Fitchburg State University. The home is lovely, with three upstairs rooms available for guests. With our family along, we spent time in two of the rooms. The Harvard is spacious and has a great shower with streams from two sides. What a luxurious experience! The Hudson is also roomy with a serene view of the pool and the back woods (and chicken coop!). It has a jetted tub, so very relaxing, and a shower too. The beds are huge and comfortable, with what must be a pillow-top on the tall firm mattress. These might be the most comfortable rooms we've ever stayed in at a B&B! Breakfast is freshly made with several delicious options from a menu where you make you selections the night before. The eggs are fresh from their own chickens! The hosts Sarah and Ryan served us in a well-lit "Florida Room" with a view of the flower-garden. And we saw a hummingbird flitting among pink and lavender flowers! On the first floor, in addition to the breakfast room, there's a kitchenette with complimentary beer and soft drinks and snack bars, single-serve coffees, and tea bags with a hot and cold water dispenser, (and both milk and cream, thx!). There is a large comfortable sitting room, where we spent part of a pleasant evening with the friendly owners, swapping travel stories. And from there is an enclosed brick pathway to a rec room with a nice billiard table. To the left is the clean outdoor pool, or ahead is the open covered lighted porch with a ceiling fan, which has a step down to the pool. We took a few laps, then walked down and around to the patio with a fire-pit and a large jacuzzi. On an overcast September day, the pool was cool but not chilly, and the jacuzzi was warm with easy-to-adjust powerful jets. The chicken coop is hidden downhill a bit further, and there's no resident rooster so you might hear some cheerful clucking but no raucous crowing. It's just 1.5h by MBTA train from North Station in Boston to this tranquil hideaway. The hosts are charming and hard-working, always making improvements, always ready with friendly conversation. The price is of course a bit more than some local hotels, but not at all expensive, and our envious hotel-staying relatives all came by for a relaxing evening of wine on the porch.

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Howarth House Bed and Breakfast - Hudson Room

Hudson Room

Howarth House Bed and Breakfast - Winter is in full force here.  Come join us for a ski weekend!

Winter is in full force here. Come join us for a ski weekend!

Howarth House Bed and Breakfast - Breakfast is served in the bright Florida Room, with a view of the flower garden, pool, and the occasional hummingbird!

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Breakfast is served in the bright Florida Room, with a view of the flower garden, pool, and the occasional hummingbird!

The Round House - guesthouses - Updated October 2026

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