Hi Again, Tess!
With Rick's space restriction , will limit this to hotel advice...
You are right -- FAR too early to book 14 Months ahead! -- Sept 2018. Right ow family-owned hotels (small office staff) are busy-busy with the High Season Flood of July-Aug. September is the "cool-down" phase, to tidy things & tend to their own lives (children into school, Athens MD appts). Also, they don't yet know what rates they'll need to set for 2018. My guess is that October they'll be ready to handle your booking request.
With this gift of time, use it wisely. Don't go thru booking.com etc -- contact hotels directly. They'll be pleased -- this saves them the 5% agency charge. Also, direct contact lets you foster a bond with them. Newcomers don't yet understand that, for Greek family-run places, this is not just business, it's personal. They interact on a human & genuine level with those who write showing a love of Greece and appreciation for their special isle or area.
This approach that has worked splendidly for me: On hotel websites, do NOT use a fill-out form... instead, use the e-mail. Write a fairly formal letter (Greeks value manners) Starting "Dear (name if possible)", Owner/Manager, Hotel XX. Begin by expressing enthusiasm for visiting their beautiful island, what praise you've heard about their place. Then ask if they may have room for 3 couples who are excited about a wonderful stay with them, as the highlight of your First trip to Naxos & Greece. Say you realize t it's too early to confirm bookings for September 2018, but by writing early, you hope we'll be first in line for 3 of your wonderful rooms (ideally with sea-view balconies or patios). Say you trust they'll get back to you right after busy season with info on 2018 rates and room-list Say that upon learning re rooms/rates you'll immediately confirm, providing credit-card information to secure reservations ("although you plan to pay in cash during your stay"-- they LOVE that). Close by wishing them a happy August 15th holiday** [Aug 15 is 2nd biggest Greek holiday of entire year, after Easter]and you look forward to their reply. . When I've written such letters "cold" (usually January, for a May trip), I've ALWAYS received warm & friendly responses ... and SO often it's led to terrific stays, and repeated visits to small hotels, & lasting friendships. My Naxos landlady meets me at ferry w. hugs & kisses, we share family photos, snacks & laughs galore.
Early September is still mainly considered High season, so rates are higher than May-June, but on Naxos, way less than Santorini or Mykonos!!! As for St. George hotels with pools ... it's hard to get one right beach, for historic reasons. When Naxos first began developing tourism, it was for the budget traveler, so most property directly on the sand has small 3-story family-run places with 10 -30 rooms, sea views, few with pools. Thus, when an upscale market developed, not much room for pool hotels... OF more than 100 hotels probably 20 w. pools total, many far from sands.
Overview: UPSCALE Hotel Nissaki, town end of beach, pool area not that attractive ... Far end: Naxos Resort Beach Hotel, back 100 yards, well Landscaped pool area MODERATE - beach Midpoint, back about 150 yards, Hotel Spiro, lovely large pool area, u need to specify to get sea-view rooms. A half-dozen others 100-150 yards off beach. These Hotel lists show which ones have pools, but vague about how close to beach: http://www.thegreektravel.com/naxos/hotels.html & http://www.naxos-island-greece.com/naxos-hotels/naxos-hotels.html Google for hotels' own websites -- if they are vague about location, may be way back. One way to check: on booking.com put "Agios Giorgios Beach Naxos" dummy booking 1 room Sept 25-29 or so, Just to access Google Map... Then click on balloons nearest beac to see if your hotel is one of them.