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    Chatham Vacation Rentals

    4.0 (4 reviews)

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    New England Vacation Rentals and Property Management

    New England Vacation Rentals and Property Management

    4.2(5 reviews)
    0.3 mi

    My wife and I renting 30 Chatham Crest Drive, Chatham, MA…read more Quite frankly, my wife and I were thrilled by the location, the exterior, the interior, the central air, the color combinations and the appointments we found on our arrival. It is a terrific house. Both Betsy and I had long associations with Chatham many years ago, before we were married. With this marvelous house as a base in such a beautiful locale, much of our expected stress has evaporated. Our very best to you, yours and your staff! We wish you continued success in your endeavors.

    This review has nothing to do with the quality of a property rented through NEVR, and everything to…read moredo with management of the property, which is entitled and unprofessional. I booked "Bay Dream" in Eastham, MA Pre-Covid with a check in time of 3pm and check out time of 10am. I did not purchase cancellation insurance as I fully intended to use the property. The $9000 fee for the 1-week rental was split into 2 payments, $4500 paid upfront and $4500 to be paid 60 days in advance of the stay. In early June I received an email that the second payment was due. As the pandemic had intensified, my wife called New England Vacation Rentals ("NEVR"), who manages the property, to see what their Covid cancellation policies were. As all reputable rental companies recognized, this was an unusual time, and most were working with their clients to cancel properties due to the pandemic. NEVR's offices were closed, and a message on the service directed us to send an email to them, which we did. By this time Massachusetts policies were that guests had to self-quarantine for 14 days, which was not possible in a 7-night stay. After 3 days we still hadn't heard from NEVR, so we emailed again. We got a reply, stating that the self-quarantine rules were "not enforceable" and that our only option to cancel was to forfeit our $4500 deposit. As this was not an option for us, we pressed on and paid the remaining $4500. Guidance around travel to Massachusetts and this property continued to change. The check-in time was changed from 3pm to 4pm, presumably to give the cleaning crew an extra hour to clean. The check out time was also moved up from 10am to 9am for the same reasons. Massachusetts also required a Covid test for people traveling from certain states, so we had to get tested the day before we traveled. All this is fine, and understandable under the circumstances we're all in. What transpired next is not. We arrived at the property at 3:40pm to find the house cleaned and vacant. As no one was there, any reasonable renter would assume it would be permissible to enter. 5 minutes later, the owner of the property knocked on the door, identifying herself and claiming "you're early." This was strange, but I briefly chatted with the owner and then moved on to unpacking and stocking up for the week. At check-out, we were asked to email NEVR when we had vacated the house. I did this at exactly 9am, again to accommodate for extra cleaning. Following NEVR's check out guidelines, we removed all food, trash, bagged the linens, set out the trash cans for pickup -- everything per their guidelines. We packed up the car with all luggage, locked the doors and went for one last walk at low tide, to celebrate the week. When we returned from the walk the owner was there, again, to state that check out was at 9am. We told her we were out. The cleaners weren't there, just the owner. 2 hours later, an email from NEVR was forwarded to me from the owner, who stated they did not want to rent to me again. "The house was left a mess, heavily used, they checked in early, checked out late. No need to take issue with them. Just don't want them as guests again." NEVR replied to the owner " No worries...we put him on the DO NOT RENT list" with a little smiley emoji at the end. Why they would send this to me is inexplicably unprofessional. When I questioned this, they hid behind the owner's wishes, stating that it was the owner's wishes, and not recognizing the callousness of forwarding the email, which caused my wife and I unnecessary stress and anxiety. While the check-in/out times were changed, without compensation to me, I acquiesced, only to receive blowback from both the owner and NEVR. They didn't use the extra time to do additional cleaning, they just wanted us out earlier. As for leaving the house 'a mess,' this is nonsense. We not only followed their guidelines, we exceeded them. As an owner of vacation rental properties in California, I am acutely aware of what a mess a tenant can leave. I have 25 years of messes. We did not leave a mess. Perhaps this owner shouldn't be renting their property at all. She seems to have issues letting go. What's worse is that throughout discussions with NEVR, they offered no apology. It is clear that NEVR views the relationship with their homeowners as the "customer," while renters are the "product." This is exactly the opposite of what it should be. No renter wants to deal with an owner at all. We have been renting properties on the cape for almost 30 years. This was our 12th trip. We have stayed in many houses, and used many management companies. Until this trip, we have had zero issues. None. The sad part about this is it has nothing to do with the property. It's a beautiful place. This is all about the interaction with the owner and NEVR. How unfortunate.

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    New England Vacation Rentals and Property Management
    New England Vacation Rentals and Property Management
    New England Vacation Rentals and Property Management

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    Surfside Motor Inn - Room 209

    Surfside Motor Inn

    4.0(13 reviews)
    1.8 mi
    $$

    One of the most unique places I have stayed in quite some time…read more First off, while it's not cheap, it's definitely way less expensive than everywhere else in the area - especially for having parking, being literally across the street from the beach, and being a 10-minute walk to the Main Street. You could park once and then not have to drive again for your time in Chatham. Also, it's very well equipped - the people who run the place know what people need for the beach and work hard to make it happen. There's towels, wagons, umbrellas and coolers. There's a communal fridge and an ice machine. There's a vending area for drinks and a continental breakfast and a wine hour. Also plenty of space for sitting outside and visiting with a view of the water. The beach across the street is really cute, too. The rooms themselves are quirky, but clean and workable with fast WiFi. The stairs are really steep so if you have any mobility issues at all I would recommend a first floor room. The bed was comfortable and the new AC was useful for blocking out next door neighbor noise. The bathroom was a bit weird - the sink counter was falling off the base a bit and the floor seemed soft/likely in need of replacement, but all was functional. The only really odd thing was that my room was next to a room which had a private bath not in the room but across the hallway, and the neighbors had both bathroom and bedroom doors open going back and forth as if it was their private area - I felt like I was intruding although I had to go through the hall way to enter and leave. However, it just added to the quirk!

    Came here for a wedding weekend during which the Surfside Inn did not have a deal for us, but was…read morelisted within walking distance of Chatham Bars Inn where the wedding was held. While in theory it is walking distance, the area closer to CBI did not have sidewalks, so would not actually recommend walking. However, ubers were about $10. We were able to walk into town fully on sidewalks, but decided not to at night because we have heard cars are known for speeding in the area and the streets are quite narrow. Better safe than sorry. Back to Surfside...we absolutely loved it. We truly felt like we were staying with family. Chris provided thoughtful suggestions, always asked how our outings were and chatted to us about where we were headed out to. Everything was explained super thoroughly. We felt very safe and welcome. Breakfast (continental) was provided, which most hotels didn't seem to do - had basics like coffee and tea, oatmeal, hot chocolate, pastries, fruit, bagels and english muffins. They also always had granola bars around which ended up being super helpful to hold us over when we needed a snack during the day. They had a "vending machine" with a few alcoholic beverages available, as well as water, all reasonably priced. The Inn had more amenities than we expected - although not fancy, super helpful stuff like a fridge for everyone to use (we brought home leftover wine and food one night and were able to store it), beach towels, beach wagons, beach chairs, umbrellas, coolers and more all to borrow. There were two outdoor showers, a fire pit and nice porch, where happy hour was held each evening where they offered wine and cheese, which was so thoughtful! There was a business area and plenty of tables if you needed to do work. Our room had everything we needed - the only thing we would have liked is a full length mirror (hard to get ready for a wedding without one!) some type of closet (or just more wall hooks) and a few more drawers to put things away. Other than that, the bed was comfortable and clean, bathroom was standard and also clean, basic toiletries were provided and we had a table with chairs, hangers, night stands with big drawers and laps and working AC! Truly almost everything we needed. Would also love a pool, but I know that's asking a bit much! Something to consider down the line maybe. You could definitely hear other guests (for example, a baby crying in the next room), but people were definitely respectful of quiet time and there was no rowdiness. Something to keep in mind is that it's listed as 2-2.5 stars, which many people think reflects things like cleanliness and related aspects. Hotel star ratings rate what the hotel provides, from basic, no frills, a place to put your head down and shower to luxurious amenities. The Surfside Inn provided more than enough for our stay and the vibe was very Cape Cod! Would 100% come back - Thank you Chris for our great stay!

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    Surfside Motor Inn
    Surfside Motor Inn - Room 209

    Room 209

    Surfside Motor Inn

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    Chatham Guest Rooms - Enjoy the spacious accommodations in a farmhouse from the 1770's that has been fully restored in the last 5 years.

    Chatham Guest Rooms

    5.0(5 reviews)
    0.2 mi

    A home away from home in Chatham:…read more We loved our recent stay in Chatham and especially staying at the Chatham Guest Rooms. We stayed in the upstairs 'Main Suite' which was spacious and comfortable for our family of 4! We really enjoyed having a full kitchen to cook in and a washer and dryer too! The apartment also came with everything we needed to enjoy the beach: chairs, towels, umbrellas, and a beach tote to carry everything in. This really came in handy! Danielle and Bob were very welcoming and created a lovely, thoughtful vacation get-a-way for their guests in a beautifully restored historic farmhouse! Thank you!

    If you're looking for quality lodging at an affordable price on Cape Cod, I highly recommend…read moreChatham Guest Rooms. This is a house about a mile down from downtown Chatham with three "guest room" options: the Main Suite, which has a full kitchen, the Garden Suite, which has a private deck and library, and the East Room, where we stayed: a room with a private bath, queen-sized bed, and large window seat overlooking the garden that fills the rear of the property. The rooms all come equipped with coffee makers, cube fridges, and a cupboard with cups, plates, coffee filters, and other essentials. The East Room is large enough for two people, nicely decorated, and appointed with a lovely antique armoire and flat-screen TV. It has exposed ceiling beams, a cool, soothing decor palette, and soft lighting. The bathroom is modern with a glass-walled shower. My only caution is that the queen-sized bed is very soft, so be aware of that if you prefer a firm mattress. I got a peek at the Main Suite, which is gorgeous, and though we went off-season I could tell that the garden would be beautiful come springtime. This is not a B&B, but there are several options for breakfast nearby, more than that in-season. The business is run by two personable locals, Bob and Danielle, who also run a neat antique map shop that's adjacent to the rooms. They are helpful, attentive, and full of suggestions for things to see and places to dine. They allowed us our privacy while being attentive to our needs and picking up the room, and they checked on us regularly to make sure we were comfortable. Chatham is a quiet, quaint town with friendly people--not funky, more of a get-away-from-it-all type of place. The Guest Rooms are about a mile down from Chatham's downtown, which has a great locally-owned bookstore (remember those?), a neighborhood theater, and a variety of restaurants and shops. The lighthouse and beach are down there as well and make for a pleasant walk after a meal. There's a grocery store and CVS nearby. Chatham's location in the "elbow" makes it ideal for venturing out to explore other parts of the Cape. If things get too sleepy for you, the energy of Provincetown is about 75 minutes north. Cape Cod Mall is a 20-minute drive away if you tire of cute, small, locally-owned businesses and just want Starbucks and a movie with Dolby Surround Sound. Finally, the price is good, especially for the Cape where even off season B&B's and inns can be pricy. The local guide Bob and Danielle gave us reported that the Guest Rooms are one of the most reasonably-priced accommodations in the area. The Main Suite was priced about the same as a 3-star hotel room in a city and had much more to offer. For what we would have paid to stay at a flea-bag hotel, we had a great experience in a clean, comfortable, personally-appointed setting. .

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    Chatham Guest Rooms - The 2 room Garden Suite includes a living room, private deck and separate entrance.

    The 2 room Garden Suite includes a living room, private deck and separate entrance.

    Chatham Guest Rooms - The owners look forward to sharing their knowledge of the area with you to ensure that you enjoy yourselves year around.

    The owners look forward to sharing their knowledge of the area with you to ensure that you enjoy yourselves year around.

    Chatham Guest Rooms - Each unit includes a sitting area, private bathroom, mini refrigerator and access to the gardens.

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    Each unit includes a sitting area, private bathroom, mini refrigerator and access to the gardens.

    Pilgrim Village - Real Sunset on pond

    Pilgrim Village

    3.0(2 reviews)
    0.2 mi

    STAY AWAY! Dont waste your money and time with this dump of a place. It's been in business for many…read moreyears and is on a nice pond, but the owner has not a clue about cutomer service, cutomer expectations and the need for clean, well maintained, child safe envirenment. There are so many other viable options in the Cape than this dump. These cottages are all outdated, undercapitalized and the lack of care that is put into the facility is glaringly apparent if you were to ever deal with the owener.

    My son is the 5th generation to stay at Pilgrim Village. That should tell you a lot- an ideal and…read moreaffordable setting for a family vacation located within easy walking or biking distance to a number of beautiful beaches, the town of Chatham, shopping and restaurants. Chatham is one of the last bastions of civilization. The town is beautiful, the people friendly, and everybody seems ecstatic to be there. The 4th of July parade is a real slice of Americana- a gesture back to a simpler time. I've travelled to almost every state and a long list of countries, but Chatham and Pilgrim Village top the list of places that make my blood pressure drop and a smile to my face. My 7 yr old son has a blast, and I feel comfortable that he is always safe riding his bike by himself through the community, meeting a bunch of kids his age, going to the playground or shuffleboard court. We never worry about him, and when we leave the community we don't even think about locking our cabin. The tranquil beach on White Pond has the cleanest water I've ever seen, is full of fish, rowboats are provided, and just sitting by it lowers your blood pressure by 30 points. If you want a 5-star hotel with mints on your pillow every night, this is not the place. But if you like a mildly rustic, relaxed atmosphere, a place where you can bring an entire family for a week for less than a thousand bucks a week, want the option to cook in your cabin rather than bear the expense of eating 3 meals a day at restaurants, this is the place for you. The Swenson family has run the place forever, are infinitely helpful, and really care about the beautiful grounds. Their daughter, son-in-law and son are taking over, and bringing new ideas to the mix like wifi, Sunday s'mores cookouts and 4th of July fireworks at the beach. One other reviewer spoke of the "draconian rules". I don't know what he was up to, but I've never experienced anything like that. If you are single, a couple, or a family, I highly recommend Pilgrim Village. Most of the visitors have made it a tradition. Many, like me, have been coming here for decades. We stay for 2 weeks each year. At this price, an extended stay is totally doable. Try staying at the Chatham Bars for that long. You'll have to take out a 2nd mortgage! ENJOY!

    Photos
    Pilgrim Village - Living room

    Living room

    Pilgrim Village - 2nd pond

    2nd pond

    Pilgrim Village - View of beach

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    View of beach

    Chatham Vacation Rentals - vacation_rentals - Updated May 2026

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